JP2017512835A - Pesticide active heterocyclic derivatives with sulfur-containing substituents - Google Patents

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1 and the agrochemically acceptable salts, stereoisomers, enantiomers of these compounds , Tautomers and N-oxides can be used as insecticides and can be prepared in a manner known per se.

Description

  The present invention relates to insecticidally active heterocyclic derivatives containing sulfur substituents, methods for their preparation, compositions containing these compounds, and animal pests (arthropods, in particular insects or It relates to their use for controlling Acarina).

  Heterocyclic compounds having a pesticidal action are known and are described, for example, in International Publication No. 2010/125985 and International Publication No. 2013/018928.

  Here, new pesticidal active heterocyclic imidazole derivatives having sulfur-containing phenyl- and pyridyl substituents have been discovered.

（式中、
Ｇ₁が、窒素又はＣＲ₂であり；
Ｇ₂が、窒素又はＣＲ₃であり；
Ｇ₃が、窒素又はＣＲ₄であり；
Ｇ₄が、窒素又はＣＲ₅であり；
Ｇ₅が、窒素又はＣＲ₆であり、ただし、Ｇとして２個以下の窒素が、連続して続いてもよく；
Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅又はＲ₆が、互いに独立して、水素、ハロゲン、Ｃ₁〜Ｃ₄ハロアルキル、１つ又は２つのヒドロキシで置換されるＣ₁〜Ｃ₄ハロアルキル、１つ又は２つのメトキシで置換されるＣ₁〜Ｃ₄ハロアルキル、１つ又は２つのシアノで置換されるＣ₁〜Ｃ₄ハロアルキルであり；又は
Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅又はＲ₆が、互いに独立して、Ｃ₁〜Ｃ₄ハロアルキルチオ、Ｃ₁〜Ｃ₄ハロアルキルスルフィニル、Ｃ₁〜Ｃ₄ハロアルキルスルホニル、Ｏ（Ｃ₁〜Ｃ₄ハロアルキル）、ＳＦ₅、フェニルカルボニルチオ、シアノ、メルカプト、Ｃ₁〜Ｃ₄アルコキシカルボニル、Ｃ₁〜Ｃ₄アルキルカルボニル又はＣ（Ｏ）Ｃ₁〜Ｃ₄ハロアルキルであり；又は
２つの隣接するＲ_i（ここで、Ｒ_iが、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅及びＲ₆から選択される）が、一緒になって、断片−ＯＣＨ₂Ｏ−又はＯＣＦ₂Ｏ−を形成してもよく；
Ｑが、式Ｑ₁及びＱ₂

からなる群から選択される基であり、
ここで、矢印がイミダゾール環への結合点を示し；
Ｘが、Ｓ、ＳＯ又はＳＯ₂であり；
各Ｒが、互いに独立して、水素、ハロゲン、Ｃ₁〜Ｃ₄ハロアルコキシ又はＣ₁〜Ｃ₄ハロアルキルであり；
各Ｒ₁が、互いに独立して、Ｃ₁〜Ｃ₄アルキル、Ｃ₁〜Ｃ₄ハロアルキル、Ｃ₃〜Ｃ₆シクロアルキル、Ｃ₃〜Ｃ₆シクロアルキル−Ｃ₁〜Ｃ₄アルキル、Ｃ₃〜Ｃ₆ハロシクロアルキル、Ｃ₂〜Ｃ₆アルケニル、Ｃ₂〜Ｃ₆ハロアルケニル又はＣ₂〜Ｃ₆アルキニルであり；
各Ｒ₇が、互いに独立して、水素又はハロゲンであり；
Ｒ₈が、水素、Ｃ₁〜Ｃ₄アルキル又はＣ₁〜Ｃ₄ハロアルキルであり；及び
Ｒ₉が、水素、Ｃ₁〜Ｃ₄アルキル、Ｃ₁〜Ｃ₄ハロアルキル又はハロゲンである）の化合物であって；
化合物２−［５−メチル−４−（３−ピリジル）−１Ｈ−イミダゾール−２−イル］−３−メチルスルファニル−ピリジンを除く化合物、ならびにそれらの化合物の農芸化学的に許容できる塩、立体異性体、鏡像異性体(enantiomer)、互変異性体及びＮ−オキシドに関する。 Accordingly, the present invention provides compounds of formula I

(Where
G ₁ is nitrogen or CR ₂ ;
G ₂ is nitrogen or CR ₃ ;
G ₃ is nitrogen or CR ₄ ;
G ₄ is nitrogen or CR ₅ ;
G ₅ is nitrogen or CR ₆ , provided that no more than 2 nitrogens may follow as G;
_{R 2, R 3, R 4} , R 5 or R _6, independently of one another, hydrogen, halogen, C ₁ -C ₄ haloalkyl, one or two C ₁ -C ₄ haloalkyl substituted with hydroxy, 1 one or C ₁ -C ₄ haloalkyl substituted with two methoxy, C ₁ -C ₄ haloalkyl substituted with one or two cyano; or _{R 2, R 3, R 4} , R 5 or R ₆ but independently of one another, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, O (C ₁ ~C ₄ haloalkyl), SF _5, phenylcarbonyl thio, cyano, Mercapto, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylcarbonyl or C (O) C ₁ -C ₄ haloalkyl; or two adjacent R _i, where R _i is R ₂ , R _{2 3,} R _4, R ₅ and R ₆ Al is selected), together, fragments -OCH ₂ O-or may form a OCF ₂ O-;
Q is the formula Q ₁ and Q ₂

A group selected from the group consisting of:
Where the arrow indicates the point of attachment to the imidazole ring;
X is S, SO or SO ₂ ;
Each R is, independently of one another are hydrogen, halogen, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkyl;
Each R ₁ independently of _one another is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C _3- C ₆ halocycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl or C ₂ -C ₆ alkynyl;
Each R ₇ is, independently of one another, hydrogen or halogen;
R ₈ is hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; and R ₉ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or halogen) There;
Compound 2- [5-methyl-4- (3-pyridyl) -1H-imidazol-2-yl] -3-methylsulfanyl-pyridine, as well as agrochemically acceptable salts and stereoisomerism of these compounds , Enantiomers, tautomers and N-oxides.

Compounds of formula I having at least one basic center are for example acid addition salts, such as strong inorganic acids such as mineral acids such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acid. Acid addition salts with, strong organic carboxylic acids such as C ₁ -C ₄ alkane carboxylic acids which are unsubstituted or substituted eg with halogens such as acetic acid such as saturated or unsaturated dicarboxylic acids such as oxalic acid, malonic acid , Succinic acid, maleic acid, fumaric acid or phthalic acid, for example hydroxycarboxylic acid, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or for example acid addition salts with benzoic acid, or organic sulfonic acids, for example unsubstituted C ₁ -C ₄ alkane are substituted with or is such as halogen at - or arylsulfonic acids, for example methane - or p- DOO It can form acid addition salts with toluenesulfonic acid. Compounds of formula I having at least one acidic group are, for example, salts with bases, such as inorganic salts, such as alkali metal or alkaline earth metal salts, such as sodium, potassium or magnesium salts, or ammonia or organic amines. Salts such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines such as ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines For example, mono-, di- or triethanolamine can be formed.

  Alkyl groups present in the definition of substituents can be linear or branched, eg, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert- Butyl, pentyl, hexyl, nonyl, decyl and their branched isomers. Alkoxy, alkenyl and alkynyl groups are derived from the mentioned alkyl groups. Alkenyl and alkynyl groups can be mono- or polyunsaturated.

  Halogen is generally fluorine, chlorine, bromine or iodine. This applies correspondingly to halogens combined with other meanings such as haloalkyl or halophenyl.

  Haloalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1 -Difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and Dichlorofluoromethyl.

  The alkoxy group preferably has a preferred chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, as well as the isomeric pentyloxy and hexyloxy groups; preferably methoxy and ethoxy.

  The alkoxyalkyl group preferably has a chain length of 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

  Cycloalkyl groups preferably have 3 to 6 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

According to the invention, O (C ₁ -C ₄ haloalkyl) corresponds to C ₁ -C ₄ haloalkoxy. Haloalkoxy groups preferably have a chain length of 1 to 4 carbon atoms. Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy or 2,2,2-trifluoroethoxy.

According to the present invention, C ₁ -C ₄ haloalkylthio corresponds to C ₁ -C ₄ haloalkylsulfanyl. Haloalkylsulfanyl groups preferably have a chain length of 1 to 4 carbon atoms. Haloalkylsulfanyl is, for example, difluoromethylsulfanyl, trifluoromethylsulfanyl or 2,2,2-trifluoroethylsulfanyl. Similar considerations apply to the groups C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ haloalkylsulfonyl, which groups are for example trifluoromethylsulfinyl, trifluoromethylsulfonyl or 2,2,2-trifluoroethyl. Can be sulfonyl.

According to the invention, two adjacent R _i, where R _i is selected from R ₂ , R ₃ , R ₄ , R ₅ and R _6, are taken together to produce the fragment —OCH ₂ when forming O- or OCF ₂ O-, additional 5-membered dioxolane or difluoro - dioxolane ring is formed. For example, a compound of formula I (wherein G ₂ is CR ₃ , G ₃ is CR ₄ and R ₃ and R ₄ together form the fragment —OCF ₂ O—) is Would have the structure

According to the present invention, when two groups G is nitrogen group consisting of G ₁ ~G _5, together with the carbon atom to which G ₁ and G ₅ are attached, form a diazine ring. The diazine ring may be selected from the group consisting of pyrimidinyl, pyrazinyl and pyridazinyl.

In a preferred embodiment of the present invention,
_{R 2, R 3, R 4} , R 5 or R _6, independently of one another, hydrogen, halogen, C ₁ -C ₄ haloalkyl, one or two C ₁ -C ₄ haloalkyl substituted with hydroxy, 1 C ₁ -C ₄ haloalkyl substituted with one or two methoxy; or R ₂ , R ₃ , R ₄ , R ₅ or R ₆ independently of one another, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfonyl, O (C ₁ ~C ₄ haloalkyl), SF _5, phenylcarbonyl thio, cyano, mercapto, or a C ₁ -C ₄ alkoxycarbonyl;
Each R is, independently of one another are hydrogen, halogen or C ₁ -C ₄ haloalkyl;
Each R ₁ independently of _one another is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C _3- C ₆ halocycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl or C ₂ -C ₆ alkynyl.

（式中、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄、及びＧ₅が、上の式Ｉで定義されるとおりであり；Ｘ₁が、Ｓ、ＳＯ又はＳＯ₂であり；Ｒａ₁が、水素、ハロゲン又はＣ₁〜Ｃ₄ハロアルキルであり；Ｒ₁₁が、メチル、エチル、ｎ−プロピル、ｉ−プロピル又はシクロプロピルメチルであり；Ｒ₈が、式Ｉで上に定義されるとおりであり、好ましくは、メチルであり、Ｒ₉が、式Ｉで上に定義されるとおりであり、好ましくは、水素である）の化合物、ならびにそれらの化合物の農芸化学的に許容できる塩、立体異性体、鏡像異性体、互変異性体及びＮ−オキシドによって表される。 A preferred group of compounds of formula I are those of formula I-1

_{(Wherein, G 1, G 2, G} 3, G 4, and G _5, are as defined by the above formula I; X ₁ is, S, be a SO or SO _2; Ra ₁ is, Hydrogen, halogen or C ₁ -C ₄ haloalkyl; R ₁₁ is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; R ₈ is as defined above in formula I , Preferably methyl, and R ₉ is as defined above in Formula I, preferably hydrogen), as well as the agrochemically acceptable salts, stereoisomers of those compounds , Enantiomers, tautomers and N-oxides.

Also preferred are compounds of formula I-1 having G ₁ defined as N, G ₂ defined as C (CF ₃ ), and G ₃ , G ₄ and G ₅ defined as CH.

Still other preferred compounds of Formula I-1 have G ₁ defined as N, G ₃ defined as C (CF ₃ ), and G ₂ , G ₄ and G ₅ defined as CH.

Further preferred compounds of formula I-1 have G ₁ defined as N, G ₄ defined as C (CF ₃ ), and G ₂ , G ₃ and G ₅ defined as CH.

Other preferred compounds of formula I-1 has a G _1, G ₄ and G _5, G is defined as N ₂ and C (CF ₃₎ G ₃ is defined as defined as CH.

Also preferred are compounds of formula I-1 having G ₁ , G ₃ and G ₅ defined as CH, G ₂ defined as N and G ₄ defined as C (CF ₃ ).

Still other preferred compounds of formula I-1 have G ₁ , G ₄ and G ₅ defined as CH, G ₃ defined as N, and G ₂ defined as C (CF ₃ ).

Another group of preferred compounds of formula I-1 has G ₁ and G ₃ defined as N, G ₄ and G ₅ defined as CH, and G ₂ defined as C (CF ₃ ).

Other preferred compounds of formula I-1 have G ₁ and G ₄ defined as N, G ₂ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Also preferred are compounds of formula I-1 having G ₁ and G ₄ defined as N, G ₃ and G ₅ defined as CH, and G ₂ defined as C (CF ₃ ).

Still other preferred compounds of formula I-1 have G ₁ and G ₅ defined as N, G ₂ and G ₄ defined as CH, and G ₃ defined as C (CF ₃ ).

Further preferred compounds of formula I-1 have G ₁ and G ₅ defined as N, G ₃ and G ₄ defined as CH, and G ₂ defined as C (CF ₃ ).

Other preferred compounds of formula I-1 have G ₂ and G ₄ defined as N, G ₁ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Also preferred are compounds of formula I-1 having G ₁ and G ₂ defined as N, G ₄ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Still other preferred compounds of formula I-1 have G ₁ and G ₂ defined as N, G ₃ and G ₅ defined as CH, and G ₄ defined as C (CF ₃ ).

In further preferred compounds of formula 1-1, G ₁ and G ₃ are N, G ₂ and G ₅ are CH, and G ₄ is C (CF ₃ ).

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is CH or C (halogen), G ₃ is CH, G ₄ is C (CF ₃ ), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is N, G ₃ is CH, G ₄ is C (CF ₃ ) or C (CN), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is N, G ₃ is C (CF ₃ ), C (halogen) or C (CN), and G ₄ is CH and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is CH, G ₃ is N, G ₄ is C (CF ₃ ) or C (halogen), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is CH, G ₃ is C (CN), G ₄ is CH, and G ₅ is CH. .

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is C (CF ₃ ) or C (CN), G ₃ is CH, G ₄ is CH, and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is N, G ₃ is CH, G ₄ is CH, and G ₅ is C (CF ₃ ). is there.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is CH, G ₃ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C ( O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃ ) or C (halogen), G ₄ is CH, and G ₅ is CH.

In a particularly preferred group of compounds of the formula I-1, G ₁ is CH and G ₂ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃ ) or C (halogen), G ₃ is CH, G ₄ is CH, and G ₅ is CH. In said particularly preferred group of compounds of the formula I-1, R ₈ is preferably methyl and R ₉ is preferably hydrogen.

（式中、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄、及びＧ₅が、上の式Ｉで定義されるとおりであり；Ｘ₂が、Ｓ、ＳＯ又はＳＯ₂であり；Ｒａ₂が、水素、ハロゲン又はＣ₁〜Ｃ₄ハロアルキルであり；Ｒ₁₂が、メチル、エチル、ｎ−プロピル、ｉ−プロピル又はシクロプロピルメチルであり；Ｒ₈が、式Ｉで上に定義されるとおりであり、好ましくは、メチルであり、Ｒ₉が、式Ｉで上に定義されるとおりであり、好ましくは、水素である）の化合物、ならびにそれらの化合物の農芸化学的に許容できる塩、立体異性体、鏡像異性体、互変異性体及びＮ−オキシドによって表される。 Another preferred group of compounds of formula I is of formula I-2

Wherein G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are as defined in Formula I above; X ₂ is S, SO or SO ₂ ; Ra ₂ is Hydrogen, halogen or C ₁ -C ₄ haloalkyl; R ₁₂ is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; R ₈ is as defined above in formula I , Preferably methyl, and R ₉ is as defined above in Formula I, preferably hydrogen), as well as the agrochemically acceptable salts, stereoisomers of those compounds , Enantiomers, tautomers and N-oxides.

Also preferred are compounds of formula I-2 having G ₁ defined as N, G ₂ defined as C (CF ₃ ), and G ₃ , G ₄ and G ₅ defined as CH.

Still other preferred compounds of formula I-2 have G ₁ defined as N, G ₃ defined as C (CF ₃ ), and G ₂ , G ₄ and G ₅ defined as CH.

Further preferred compounds of formula I-2 have G ₁ defined as N, G ₄ defined as C (CF ₃ ), and G ₂ , G ₃ and G ₅ defined as CH.

Other preferred compounds of formula I-2 has a G _1, G ₄ and G _5, G is defined as N ₂ and C (CF ₃₎ G ₃ is defined as defined as CH.

Also preferred are compounds of formula I-2 having G ₁ , G ₃ and G ₅ defined as CH, G ₂ defined as N and G ₄ defined as C (CF ₃ ).

Still other preferred compounds of formula I-2 have G ₁ , G ₄ and G ₅ defined as CH, G ₃ defined as N, and G ₂ defined as C (CF ₃ ).

Another group of preferred compounds of formula I-2 have G ₁ and G ₃ defined as N, G ₄ and G ₅ defined as CH, and G ₂ defined as C (CF ₃ ).

Other preferred compounds of formula I-2 have G ₁ and G ₄ defined as N, G ₂ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Also preferred are compounds of formula I-2 having G ₁ and G ₄ defined as N, G ₃ and G ₅ defined as CH, and G ₂ defined as C (CF ₃ ).

Still other preferred compounds of formula I-2 have G ₁ and G ₅ defined as N, G ₂ and G ₄ defined as CH, and G ₃ defined as C (CF ₃ ).

Further preferred compounds of formula I-2 have G ₁ and G ₅ defined as N, G ₃ and G ₄ defined as CH, and G ₂ defined as C (CF ₃ ).

Other preferred compounds of formula I-2 have G ₂ and G ₄ defined as N, G ₁ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Also preferred are compounds of formula I-2 having G ₁ and G ₂ defined as N, G ₄ and G ₅ defined as CH, and G ₃ defined as C (CF ₃ ).

Still other preferred compounds of formula I-2 have G ₁ and G ₂ defined as N, G ₃ and G ₅ defined as CH, and G ₄ defined as C (CF ₃ ).

In further preferred compounds of formula I-2, G ₁ and G ₃ are N, G ₂ and G ₅ are CH, and G ₄ is C (CF ₃ ).

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is CH or C (halogen), G ₃ is CH, G ₄ is C (CF ₃ ), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is N, G ₃ is CH, G ₄ is C (CF ₃ ) or C (CN), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-2, G ₁ is CH, G ₂ is N, G ₃ is C (CF ₃ ), C (halogen) or C (CN), and G ₄ is CH and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is CH, G ₃ is N, G ₄ is C (CF ₃ ) or C (halogen), and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is CH, G ₃ is C (CN), G ₄ is CH, and G ₅ is CH. .

In a particularly preferred group of compounds of formula I-1, G ₁ is N, G ₂ is C (CF ₃ ) or C (CN), G ₃ is CH, G ₄ is CH, and G ₅ is CH.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is N, G ₃ is CH, G ₄ is CH, and G ₅ is C (CF ₃ ). is there.

In a particularly preferred group of compounds of formula I-1, G ₁ is CH, G ₂ is CH, G ₃ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C ( O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃ ) or C (halogen), G ₄ is CH, and G ₅ is CH.

In a particularly preferred group of compounds of the formula I-1, G ₁ is CH and G ₂ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃ ) or C (halogen), G ₃ is CH, G ₄ is CH, and G ₅ is CH. In said particularly preferred group of compounds of the formula I-1, R ₈ is preferably methyl and R ₉ is preferably hydrogen.

（式中、
Ａが、Ｎ又はＣＨであり；
Ｒ₁₀が、ハロゲン、シアノ、Ｃ₁〜Ｃ₄ハロアルコキシ、Ｃ₁〜Ｃ₄ハロアルキル及びＣ₁〜Ｃ₄アルキルカルボニルからなる群から独立して選択される置換基で一置換又は多置換されるフェニルであり；又は
Ｒ₁₀が、Ｃ₁〜Ｃ₄ハロアルキルスルファニル、Ｃ₁〜Ｃ₄ハロアルキルスルフィニル及びＣ₁〜Ｃ₄ハロアルキルスルホニル、特に、トリフルオロメチルスルファニル、トリフルオロメチルスルフィニル及びトリフルオロメチルスルホニルからなる群から独立して選択される置換基で一置換されるフェニルであり；又は
Ｒ₁₀が、２つの隣接する位置において断片−ＯＣＦ₂Ｏ−で置換されるフェニルであり；又は
Ｒ₁₀が、ハロゲン、シアノ、Ｃ₁〜Ｃ₄ハロアルコキシ、Ｃ₁〜Ｃ₄ハロアルキル及びＣ₁〜Ｃ₄アルキルカルボニルからなる群から独立して選択される置換基で一置換又は多置換されるピリジルであり；又は
Ｒ₁₀が、Ｃ₁〜Ｃ₄ハロアルキルスルファニル、Ｃ₁〜Ｃ₄ハロアルキルスルフィニル及びＣ₁〜Ｃ₄ハロアルキルスルホニル、特に、トリフルオロメチルスルファニル、トリフルオロメチルスルフィニル及びトリフルオロメチルスルホニルからなる群から独立して選択される置換基で一置換されるピリジルであり；又は
Ｒ₁₀が、２つの隣接する位置において断片−ＯＣＦ₂Ｏ−で置換されるピリジルであり；
Ｘ₃が、Ｓ、ＳＯ又はＳＯ₂、特に、Ｓ又はＳＯ₂であり；
Ｒａ₃が、水素又はＣ₁〜Ｃ₄ハロアルキル、特に、トリフルオロメチルであり；
Ｒ₁₃が、Ｃ₁〜Ｃ₄アルキル、特に、メチル又はエチルであり；
Ｒ₈が、水素又はＣ₁〜Ｃ₄アルキル、特に、メチル又はエチルであり；
Ｒ₉が、水素、Ｃ₁〜Ｃ₄アルキル又はハロゲン、特に、水素、塩素又はメチルである）の化合物、ならびに式Ｉ−３の化合物の農芸化学的に許容できる塩、立体異性体、鏡像異性体、互変異性体及びＮ−オキシドによって表される式Ｉの化合物を含む。 A further preferred embodiment of the present invention is a compound of formula I-3

(Where
A is N or CH;
R ₁₀ is mono- or polysubstituted with a substituent independently selected from the group consisting of halogen, cyano, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkylcarbonyl. Or R ₁₀ is from C ₁ -C ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ haloalkylsulfonyl, in particular trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl. Or phenyl that is monosubstituted with a substituent independently selected from the group consisting of: or R ₁₀ is phenyl that is substituted at two adjacent positions with the fragment —OCF ₂ O—; or R ₁₀ is halogen, cyano, C ₁ -C ₄ haloalkoxy, from C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkylcarbonyl That with substituents independently selected from the group be mono- or polysubstituted by pyridyl; or R ₁₀ is, C ₁ -C ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ haloalkyl Sulfonyl, in particular pyridyl monosubstituted with substituents independently selected from the group consisting of trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl; or R ₁₀ is in two adjacent positions fragment -OCF pyridyl substituted ₂ O- in;
X ₃ is S, SO or SO ₂ , in particular S or SO ₂ ;
Ra ₃ is hydrogen or C ₁ -C ₄ haloalkyl, in particular trifluoromethyl;
R ₁₃ is C ₁ -C ₄ alkyl, in particular methyl or ethyl;
R ₈ is hydrogen or C ₁ -C ₄ alkyl, in particular methyl or ethyl;
R ₉ is hydrogen, C ₁ -C ₄ alkyl or halogen, in particular hydrogen, chlorine or methyl), and agrochemically acceptable salts, stereoisomers, enantiomers of compounds of formula I-3 And compounds of formula I represented by tautomers, tautomers and N-oxides.

In said preferred embodiments comprising compounds of formula I-3, R ₁₀ is preferably halogen, cyano, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C is a ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ phenyl or pyridyl is monosubstituted with a substituent selected independently from the group consisting haloalkylsulfonyl. Particularly preferred R ₁₀ is selected from fluorine, chlorine, cyano, difluoromethoxy, trifluoromethoxy, trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl and trifluoromethylsulfonyl.

（式中、
Ａが、Ｎ又はＣＨであり；
Ｒ₁₀’が、式ＤＡ１〜ＤＡ５

からなる群から選択されるジアジン基であり、ここで、矢印が、トリアゾール環への結合点を示し、及び前記基Ｒ₁₀’が、ハロゲン、シアノ、Ｃ₁〜Ｃ₄ハロアルコキシ及びＣ₁〜Ｃ₄ハロアルキルからなる群から独立して選択される置換基で一置換又は多置換されてもよく；
Ｘ₄が、Ｓ、ＳＯ又はＳＯ₂、特に、Ｓ又はＳＯ₂であり；
Ｒａ₄が、水素又はＣ₁〜Ｃ₄ハロアルキル、特に、トリフルオロメチルであり；
Ｒ₁₄が、Ｃ₁〜Ｃ₄アルキル、特に、メチル又はエチルであり；
Ｒ₈が、水素又はＣ₁〜Ｃ₄アルキル、特に、メチル又はエチルであり；
Ｒ₉が、水素、Ｃ₁〜Ｃ₄アルキル又はハロゲン、特に、水素、塩素又はメチルである）の化合物、ならびに式Ｉ−４の化合物の農芸化学的に許容できる塩、立体異性体、鏡像異性体、互変異性体及びＮ−オキシドによって表される式Ｉの化合物を含む。 A further preferred embodiment of the present invention is a compound of formula I-4

(Where
A is N or CH;
R ₁₀ 'is a formula DA1-DA5

A diazine group selected from the group consisting of: wherein the arrow indicates the point of attachment to the triazole ring, and the group R ₁₀ ′ is halogen, cyano, C ₁ -C ₄ haloalkoxy and C _1- May be mono- or poly-substituted with a substituent independently selected from the group consisting of C ₄ haloalkyl;
X ₄ is S, SO or SO ₂ , in particular S or SO ₂ ;
Ra ₄ is hydrogen or C ₁ -C ₄ haloalkyl, in particular trifluoromethyl;
R ₁₄ is C ₁ -C ₄ alkyl, in particular methyl or ethyl;
R ₈ is hydrogen or C ₁ -C ₄ alkyl, in particular methyl or ethyl;
R ₉ is hydrogen, C ₁ -C ₄ alkyl or halogen, especially hydrogen, chlorine or methyl), and agrochemically acceptable salts, stereoisomers, enantiomers of compounds of formula I-4 And compounds of formula I represented by tautomers, tautomers and N-oxides.

In said preferred embodiments comprising a compound of formula I-4, R ₁₀ ′ is preferably independently selected from the group consisting of halogen, cyano, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ halo-alkyl. A diazine group selected from the group consisting of the formulas DA1 to DA5 that are monosubstituted with a substituent. Particularly preferred are substituents selected from fluorine, chlorine, cyano, difluoromethoxy, trifluoromethoxy, trifluoromethyl and pentafluoroethyl. Still other preferred compounds of formula I-4 have R ₁₀ 'defined as DA5, where R ₁₀ ' is halogen, cyano, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkyl. From the group consisting of, in particular, monosubstituted with a substituent independently selected from fluorine, chlorine, cyano, difluoromethoxy, trifluoromethoxy, trifluoromethyl and pentafluoroethyl.

The process according to the invention for preparing the compounds of the formula I is in principle carried out by methods known to those skilled in the art. More particularly, a subgroup of compounds of the formula I (wherein X is SO (sulfoxide) and / or SO ₂ (sulfone)) is, for example, among other oxidizing agents, particularly m-chloroperoxide. Correspondence of formula I (where X is S), including reagents such as benzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite Obtained by oxidation reaction of sulfide compounds. The oxidation reaction is generally performed in the presence of a solvent. Examples of solvents used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of the oxidizing agent used in the reaction is generally 1 to 3 mol, preferably 1 to 1.2 mol, based on 1 mol of the sulfide compound I for producing the sulfoxide compound I. Preferably, there are 2 to 2.2 moles of oxidant for 1 mole of sulfide compound I to produce. Such an oxidation reaction is disclosed, for example, in International Publication No. 2013/018928.

を表し、ここで、Ｊの左への矢印が、断片

への結合点を示し、Ｊの右への矢印が、基Ｑへの結合点を示し；Ｒ₈及びＲ₉が、上の式Ｉで定義されるとおりである。 In the scheme below, group J is a group

Where the arrow to the left of J is the fragment

And the arrow to the right of J indicates the point of attachment to the group Q; R ₈ and R ₉ are as defined in Formula I above.

（式中、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄、Ｇ₅、Ｊ及びＱが上に定義されるとおりである）の化合物は、遷移金属−触媒反応によって、式ＩＩ

（式中、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄及びＧ₅が上に定義されるとおりであり、Ｒ’’が、例えば水素（その場合、式ＩＩの化合物はボロン酸である）又はＣ₁〜Ｃ₄アルキル（ボロン酸エステル）である）の化合物を、式ＩＩＩ

（式中、Ｊ及びＱが上に定義されるとおりであり、Ｌ_Gが、ハロゲン、好ましくは、臭素又はヨウ素、又はＣ_1~4ハロアルキルスルホネート、特にトリフレートなどの擬ハロゲンである）の化合物と反応させることによって調製され得る。実際には、式ＩＩのボロン酸、又はその好適な塩又はエステルは、例えば鈴木−宮浦条件などのパラジウム−又はニッケル−触媒条件下で、式ＩＩＩの化合物と反応する。このようなクロスカップリング反応は、任意選択的にマイクロ波照射下で、２５〜２００℃、好ましくは、５０〜１５０℃の温度で、テトラヒドロフラン、Ｎ，Ｎ−ジメチルホルムアミド、ジオキサン又は１，２−ジメトキシエタンなど、又は１，２−ジメトキシエタン−水混合物などの不活性溶媒中で、炭酸ナトリウム、炭酸カリウム又は炭酸セシウムなどの塩基の存在下で行われる。例えば［１，１−ビス（ジフェニルホスフィノ）フェロセン］ジクロロパラジウム（ＩＩ）（ＰｄＣｌ₂（ｄｐｐｆ））又はビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド（ＰｄＣｌ₂（ＰＰｈ₃）₂）などの、様々な金属、触媒及びリガンドが、この反応タイプに使用され得る。このような変換のための反応条件及び触媒系が、例えば、国際公開第０８／０７１４０５号パンフレットに記載されている。式タイプＩＩの代替的なホウ素系試薬は、２，３−ジメチル−２，３−ブタンジオール（ＩＩａ）、２，２−ジメチル−１，３−プロパンジオール（ＩＩｂ）、及び１，３−プロパンジオール（ＩＩｃ）、及び有機トリフルオロボレート、例えばカリウムトリフルオロボレート（ＩＩｄ）などのＩＩと類似の塩から誘導されるボロン酸エステル（ｂｏｒｏｎｉｃ ｅｓｔｅｒ）（ボロン酸エステル（ｂｏｒｏｎａｔｅ ｅｓｔｅｒ）とも呼ばれる）を含み得る。

Formula I

Compounds of the formula (wherein G ₁ , G ₂ , G ₃ , G ₄ , G ₅ , J and Q are as defined above) can be converted to compounds of formula II by transition metal-catalyzed reaction.

Wherein G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are as defined above, and R ″ is for example hydrogen (in which case the compound of formula II is a boronic acid) or A compound of C ₁ -C ₄ alkyl (which is a boronic ester) is represented by formula III

(Is as in formula, J and Q are defined above, L _G is halogen, preferably, bromine or iodine, or C _{1 ~ 4} haloalkylsulfonate, in particular pseudohalogen such as triflate) compound of Can be prepared by reacting with. In practice, a boronic acid of formula II, or a suitable salt or ester thereof, reacts with a compound of formula III under palladium- or nickel-catalyzed conditions such as, for example, Suzuki-Miyaura conditions. Such a cross-coupling reaction is optionally carried out under microwave irradiation at a temperature of 25-200 ° C., preferably 50-150 ° C., tetrahydrofuran, N, N-dimethylformamide, dioxane or 1,2- It is carried out in the presence of a base such as sodium carbonate, potassium carbonate or cesium carbonate in an inert solvent such as dimethoxyethane or a 1,2-dimethoxyethane-water mixture. For example, [1,1-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (PdCl ₂ (dppf)) or bis (triphenylphosphine) palladium (II) dichloride (PdCl ₂ (PPh ₃ ) ₂ ), Various metals, catalysts and ligands can be used for this reaction type. Reaction conditions and catalyst systems for such conversion are described, for example, in WO08 / 071405. Alternative boron-based reagents of formula type II are 2,3-dimethyl-2,3-butanediol (IIa), 2,2-dimethyl-1,3-propanediol (IIb), and 1,3-propane Including diol (IIc) and boronic ester (also called boronate ester) derived from salts similar to II such as organic trifluoroborate, eg potassium trifluoroborate (IId) obtain.

（式中、Ｑ及びＲ₈が、上の式Ｉで定義されるとおりであり、Ｌ_Gが、ハロゲン、好ましくは、ヨウ素又は臭素であり、Ｒ₉が、好ましくは、水素である）の化合物は、新規であり、特に、本発明の式Ｉの化合物の調製のために開発されたものである。したがって、式（ＩＩＩａ）の化合物は、本発明のさらなる対象である。式Ｉの化合物についての好ましい置換基の定義は、式（ＩＩＩａ）の化合物についても有効である。 Formula (IIIa)

(Wherein, Q and R ₈ are, are as defined in above formula I, L _G is halogen, preferably iodine or bromine, R ₉ is preferably hydrogen and a) compounds of Are new and in particular have been developed for the preparation of the compounds of the formula I according to the invention. Accordingly, compounds of formula (IIIa) are a further subject of the present invention. Preferred substituent definitions for compounds of formula I are also valid for compounds of formula (IIIa).

（式中、Ｊ及びＱが上に定義されるとおりであり、Ｌ_Gが、ハロゲン、好ましくは、臭素又はヨウ素である）の化合物は、式ＩＶ

（式中、Ｊ及びＱが上に定義されるとおりである）の化合物を、Ｎ−クロロスクシンイミド（ＮＣＳ）、Ｎ−ブロモスクシンイミド（ＮＢＳ）又はＮ−ヨードスクシンイミド（ＮＩＳ）、あるいは塩素、臭素又はヨウ素などの試薬と反応させることによって調製され得る。このようなハロゲン化反応は、例えば、Ｋ．Ｇ．Ｈｏｌｄｅｎ ｅｔ ａｌ．，Ｊ．Ｏｒｇ．Ｃｈｅｍ．２００２，６７，５９１３−５９１８に記載されているように、２５〜２００℃、好ましくは、２５〜１００℃の温度で、クロロホルム、四塩化炭素、１，２−ジクロロエタン、酢酸、エーテル、アセトニトリル又はＮ，Ｎ−ジメチルホルムアミドなどの不活性溶媒中で行われる。 Formula III

(Is as in formula, J and Q are defined above, L _G is halogen, preferably, bromine or iodine in a) a compound of the formula IV

A compound of the formula (wherein J and Q are as defined above) is N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS), or chlorine, bromine or It can be prepared by reacting with a reagent such as iodine. Such halogenation reactions are described, for example, in K.K. G. Holden et al. , J .; Org. Chem. 2002, 67, 5913-5918, at a temperature of 25-200 ° C, preferably 25-100 ° C, chloroform, carbon tetrachloride, 1,2-dichloroethane, acetic acid, ether, acetonitrile or N , N-dimethylformamide.

（式中、Ｑ及びＲ₈が、上の式Ｉで定義されるとおりであり、Ｒ₉が、好ましくは、水素である）の化合物は、新規であり、特に、本発明の式Ｉの化合物の調製のために開発されたものである。したがって、式ＩＶａの化合物は、本発明のさらなる対象である。式Ｉの化合物についての好ましい置換基の定義は、式ＩＶａの化合物についても有効である。 Formula IVa

Compounds of the formula (wherein Q and R ₈ are as defined in formula I above and R ₉ is preferably hydrogen) are novel, in particular compounds of formula I according to the invention It was developed for the preparation of Accordingly, compounds of formula IVa are a further subject of the present invention. Preferred substituent definitions for compounds of formula I are also valid for compounds of formula IVa.

Formula III and IV (wherein is as J, Q and L _G are defined above, X is, SO (sulfoxides) and / or SO ₂ (sulfone)) subgroup of compounds are, for example And, among other oxidizing agents, formulas comprising reagents such as m-chloroperbenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite Obtained by the oxidation reaction of the corresponding sulfide compound of III or IV, wherein X is S (sulfide). The oxidation reaction is generally performed in the presence of a solvent. Examples of solvents used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of oxidizing agent used in the reaction is generally from 1 to 3 mol, preferably from 1 to 1.2 mol, relative to 1 mol of the sulfide compound III or IV to produce the sulfoxide compound III or IV. Preferably, there are 2 to 2.2 moles of oxidizing agent per mole of sulfide compound III or IV to produce the sulfone compound III or IV. Such an oxidation reaction is disclosed, for example, in International Publication No. 2013/018928.

（式中、Ｒ₈及びＲ₉が、式Ｉ中に記載されるとおりであり、Ｑ_aが、式Ｑ_1a〜Ｑ_2a：

（式中、Ｒ及びＲ₇が上に定義されるとおりであり、Ｘ₁₀がハロゲンである）からなる群から選択される基である）の化合物を、
式ＶＩ
Ｒ₁−ＳＨ（ＶＩ）
の化合物又はその塩（式中、Ｒ₁が、式Ｉ中に定義されるとおりである）と反応させることによって調製され得る。使用される溶媒の例としては、ＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、及び１，４−ジオキサンなどのエーテル、トルエン及びキシレンなどの芳香族炭化水素、アセトニトリルなどのニトリル又はＮ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチル−２−ピロリドン又はジメチルスルホキシドなどの極性非プロトン性溶媒が挙げられる。式ＶＩの化合物の塩の例は、式ＶＩａ
Ｒ₁−Ｓ−Ｍ（ＶＩａ）
（式中、Ｒ₁が上に定義されるとおりであり、Ｍが、例えば、ナトリウム又はカリウムである）の化合物を含む。 The compound of formula IV, wherein J and Q are as defined above and X is S (sulfide) is preferably in an inert solvent at a temperature of 25-120 ° C. Optionally, the presence of a suitable base such as alkali metal carbonates, for example sodium carbonate and potassium carbonate, or alkali metal hydrides such as sodium hydride, or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Below, the formula V

Wherein R ₈ and R ₉ are as described in Formula I, and Q _a is represented by Formulas Q _{1a to} Q _2a :

A compound selected from the group consisting of: wherein R and R ₇ are as defined above and X ₁₀ is halogen.
Formula VI
R ₁ -SH (VI)
Or a salt thereof, wherein R ₁ is as defined in Formula I. Examples of solvents used include THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, or N, N— Examples include polar aprotic solvents such as dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone or dimethyl sulfoxide. Examples of salts of compounds of formula VI are of formula VIa
R ₁ -SM (VIa)
Wherein R ₁ is as defined above and M is, for example, sodium or potassium.

の化合物又はその塩及び／又は互変異性体（式中、Ｒ₉及びＱ_aが、上述されるとおりである）を、
式
Ｒ₈−Ｌ_G2（ＶＩＩＩ）
（式中、Ｒ₈が上に定義されるとおりであり、Ｌ_G2が、ハロゲン（特に、臭素又はヨウ素）、又は脱離基ＯＳＯ₂Ｒ₃₈（ここで、Ｒ₃₈がＣ₁〜Ｃ₆アルキル、Ｃ₁〜Ｃ₆ハロアルキル、又はニトロ又はＣ₁〜Ｃ₃アルキルで任意選択的に置換されるフェニルである）（特に、メシレート、トリフレート又はトシレートなどのスルホネート）又はサルフェート（特に、Ｒ₈がメチルである場合、アルキル化剤ＶＩＩＩ硫酸ジメチルを形成する）である）のアルキル化剤と反応させることによって調製され得る。 The compound of formula V (wherein R ₈ , R ₉ and Q _a are as defined above) is at a temperature of 20-150 ° C., tetrahydrofuran, dioxane, acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone or dimethyl sulfoxide, preferably in the presence of a suitable base such as sodium hydride or sodium carbonate, potassium carbonate or cesium carbonate. VII

Or a salt and / or tautomer thereof, wherein R ₉ and Q _a are as described above.
Wherein R ₈ -L _G2 (VIII)
Wherein R ₈ is as defined above and LG ₂ is halogen (especially bromine or iodine) or leaving group OSO ₂ R ₃₈ (where R ₃₈ is C ₁ -C ₆ alkyl , C ₁ -C ₆ haloalkyl, or phenyl optionally substituted with nitro or C ₁ -C ₃ alkyl) (especially sulfonates such as mesylate, triflate or tosylate) or sulfates (especially R ₈ is In the case of methyl, it can be prepared by reacting with an alkylating agent)) which forms an alkylating agent VIII dimethyl sulfate.

のアミノアセタール試薬又はその塩（式中、Ｒ’’’がＣ₁〜Ｃ₆アルキルであり、Ｒ₉が上に定義されるとおりである）による処理により、式ＩＮＴ₂のアミジン−アセタール中間体（又はその塩及び／又は互変異性体）を生成し；続いて、
ｉｉｉ）０〜１５０℃の温度での、例えば、塩酸水溶液などによるアセタールの脱保護、及び同時の環化により、式ＶＩＩの化合物、又はその塩及び／又は互変異性体を形成することによって調製され得る。式ＩＸの化合物から式ＶＩＩの化合物を調製するための記載される方法は、中間体ＩＮＴ₁及びＩＮＴ₂、（これは、遊離塩基として又は塩（例えば、ハロゲン化水素酸塩、より詳細には、塩酸塩又は臭化水素酸塩、又は任意の他の同等の塩）として単離され得る）の単離及び精製を含み得るが、この方法は、例えば、Ｍ．Ｅ．Ｖｏｓｓ ｅｔ ａｌ．，Ｔｅｔｒａｈｅｄｒｏｎ ２００８，６４，６４５−６５１に記載されているように、ワンポット調製として有利に行われる。この方法は、Ｒ₉が水素である特定の状況についてスキーム１にまとめられている。

A compound of formula VII, or a salt and / or tautomer thereof, wherein R ₉ and Q _a are as defined above, are of formula IX
Q _a -CN (IX)
A nitrile compound of the formula (wherein Q _a is as described above)
i) A catalytic amount, preferably 0.01 to 0.5 equivalents, of an alkoxide, preferably sodium methoxide NaOMe or sodium ethoxide NaOEt in an alcohol solvent such as methanol or ethanol at a temperature of 0-100 ° C. To produce an imidate intermediate of formula INT ₁ (or a salt and / or tautomer thereof);
ii) Acidification of the reaction mixture, for example with acetic acid, and the formula X at a temperature of 0 to 150 ° C.

An amidine-acetal intermediate of formula INT ₂ by treatment with an aminoacetal reagent of formula I or an salt thereof wherein R ′ ″ is C ₁ -C ₆ alkyl and R ₉ is as defined above. (Or salts and / or tautomers thereof);
iii) prepared by forming a compound of formula VII, or a salt and / or tautomer thereof, by deprotection of the acetal, eg, with aqueous hydrochloric acid, and the like, and simultaneous cyclization at a temperature of 0-150 ° C. Can be done. The described method for preparing compounds of formula VII from compounds of formula IX is described in intermediates INT ₁ and INT ₂ , which can be used as free bases or salts (eg hydrohalides, more particularly , Hydrochloride or hydrobromide, or any other equivalent salt) can be isolated and purified, but this method can be E. Voss et al. , Tetrahedron 2008, 64, 645-651, advantageously as a one-pot preparation. This method is summarized in Scheme 1 for the specific situation where R ₉ is hydrogen.

  Alternatively, the compound of formula INT1 is an alcohol reagent such as methanol or ethanol at a temperature of -40 to 50 ° C, preferably -20 to 20 ° C, preferably in an inert solvent such as diethyl ether, tetrahydrofuran or dioxane. Typically, a compound of formula IX can be prepared by treating with a hydrohalic acid, preferably hydrochloric acid, under the conditions and variations of pinner reactions known to those skilled in the art.

Whether the compound of formula IX (wherein Qa is as described above) and the reagent of formula X (wherein R ₉ and R ′ ″ are as described above) are known compounds, Alternatively, it can be prepared by known methods described in the literature.

Alternatively, compounds of formula I can be prepared from compounds of formula V that contain the same chemical reactions as described above, except that the order of steps is changed. This alternative route is summarized in Scheme 2.

  The reactant can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxide, alkali metal or alkaline earth metal hydride, alkali metal or alkaline earth metal amide, alkali metal or alkaline earth metal alkoxide, alkali metal or alkali Earth metal acetate, alkali metal or alkaline earth metal carbonate, alkali metal or alkaline earth metal dialkylamide or alkali metal or alkaline earth metal alkylsilylamide, alkylamide, alkylenediamide, free or N-alkylated saturation Or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis (trimethylsilyl) ) Amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N, N-dimethylamine, N, N-diethylaniline, pyridine, 4- (N, N-dimethylamino) pyridine, Quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).

  The reactants can be reacted with each other as they are, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add inert solvents or diluents or mixtures thereof. If the reaction is carried out in the presence of a base, an excess of base such as triethylamine, pyridine, N-methylmorpholine or N, N-diethylaniline can also serve as a solvent or diluent.

  The reaction is advantageously carried out in a temperature range from about -80 ° C to about + 140 ° C, preferably from about -30 ° C to about + 100 ° C, often in the range from ambient temperature to about + 80 ° C.

  A compound of formula I can be converted to another compound of formula I by substituting one or more substituents of the starting compound of formula I with other substituents according to the invention in a conventional manner. It can be converted in a manner known per se.

  Depending on the choice of suitable reaction conditions and starting materials, for example, in one reaction step it is possible to simply substitute one substituent with another substituent according to the invention, or multiple substitutions The group can be substituted with other substituents according to the invention in the same reaction step.

  Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or suitable ion exchange reagent, and salts with a base are obtained by treatment with a suitable base or suitable ion exchange reagent.

  Salts of compounds of formula I can be converted, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, to acid addition salts of the free compounds I and, for example, by treatment with a suitable acid or a suitable ion exchange reagent. Can be converted to salts with bases in a conventional manner.

  The salts of the compounds of the formula I are insoluble in, for example, the inorganic salts that form silver chloride, and thus, in a suitable solvent that precipitates out of the reaction mixture, for example, the inorganic acid salts, such as hydrochlorides, sodium salts of acids, barium. Conversion in a manner known per se to other salts, acid addition salts, eg other acid addition salts of the compounds of the formula I, by treatment with a suitable metal salt, such as a silver salt or a silver salt Can be done.

  Depending on the procedure or reaction conditions, compounds of formula I with salt-forming properties are obtained in free form or in salt form.

  Compounds of formula I and optionally tautomers thereof, each appear in free or salt form, depending on the number, absolute and relative configuration of asymmetric carbon atoms present in the molecule and / or in the molecule Depending on the arrangement of the non-aromatic double bonds, for example in the form of pure isomers such as enantiomers and / or diastereomers, or enantiomeric mixtures such as racemates, diastereomeric mixtures or racemic May exist as a mixture of isomers, such as a mixture of isomers, in one form of possible isomers or as a mixture thereof; the present invention relates to pure isomers and also to all possible isomer mixtures, Even if the details of the stereochemistry are not specifically described, they should be understood in this sense above and below, respectively.

  Diastereomeric or racemic mixtures of the compounds of formula I are prepared in free or salt form, depending on which starting materials and procedures are selected, for example by fractional crystallization, distillation and / or chromatography. Based on these physicochemical differences, they can be separated into pure diastereomers or racemates by known methods.

  Enantiomeric mixtures such as racemates obtained in a similar manner can be obtained by known methods, for example by recrystallization from optically active solvents, chromatography on chiral adsorbents, for example acetylcellulose using suitable microorganisms. By high-performance liquid chromatography (HPLC), for example by cleavage with a specific immobilized enzyme via formation of an inclusion compound, using a chiral crown ether in which only one enantiomer is complexed, or diastereo By conversion to a merceric salt, for example, the basic end product racemate is reacted with an optically active acid such as a carboxylic acid, such as camphoric acid, tartaric acid or malic acid, or a sulfonic acid, such as camphorsulfonic acid, and so on. The resulting diastereomeric mixture can be fractionated, for example, based on different solubilities Separated by crystallization, a suitable material, for example by the action of a basic substance, by obtaining a diastereomer desired enantiomer can be released therefrom, it can be resolved into the optical antipodes.

  Pure diastereomers or enantiomers can be obtained not only by separating suitable isomer mixtures according to the invention, but also by generally known methods of diastereoselective or enantioselective synthesis, for example It can also be obtained by carrying out the process according to the invention using starting materials having stereochemical properties.

N-oxides can be prepared by reacting a compound of Formula I with a suitable oxidizing agent, such as H ₂ O ₂ / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidation is described, for example, in J. Org. Med. Chem. , 32 (12), 2561-73, 1989 or WO 00/15615.

  If the individual components have different biological activities, each of the biologically more effective isomers, e.g. enantiomers or diastereomers, or isomer mixtures, e.g. enantiomer mixtures or diastereomeric mixtures, is It is advantageous to separate or synthesize.

  The compounds of formula I and optionally tautomers thereof may be obtained in free or salt form, respectively, optionally in the form of hydrates, and / or other solvents such as solids Includes solvents that could be used to crystallize the compound present in form.

  The compounds represented in Tables 1-6 below may be prepared according to the methods described above. The examples that follow are intended to illustrate the invention and to show preferred compounds of formula I.

（式中、Ｘ₁がＳであり、Ｒａ₁、Ｒ₁₁、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄及びＧ₅が、以下に定義されるとおりである）の１１８種の化合物１．００１〜１．１１８及び表１の化合物のＮ−オキシドを開示する。 Table 1: This table shows the formula I-1a:

118 compounds 1.001 in which X ₁ is S and Ra ₁ , R ₁₁ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are as defined below N-oxides of the compounds of ~ 1.118 and Table 1 are disclosed.

Table 2: This table shows the formula I-1a where X ₁ is SO and Ra ₁ , R ₁₁ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are defined in Table 1. 118 compounds 2.001 to 2.118 are disclosed.

Table 3: This table shows the formula I-1a where X ₁ is SO ₂ and Ra ₁ , R ₁₁ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are defined in Table 1. 118 compounds 3.0001 to 3.118 are disclosed.

（式中、Ｘ₂がＳであり、Ｒａ₂、Ｒ₁₂、Ｇ₁、Ｇ₂、Ｇ₃、Ｇ₄及びＧ₅が、以下に定義されるとおりである）の１１８種の化合物４．００１〜４．１１８及び表４の化合物のＮ−オキシドを開示する。 Table 4: This table shows the formula I-2a:

118 compounds of formula 4.001 wherein X ₂ is S and Ra ₂ , R ₁₂ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are as defined below N-oxides of the compounds of ~ 4.118 and Table 4 are disclosed.

Table 5: This table shows the formula I-2a where X ₁ is SO and Ra ₂ , R ₁₂ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are defined in Table 4 118 compounds of 5.001-5.118 are disclosed.

Table 6: This table shows the formula I-2 (wherein X ₁ is SO ₂ and Ra ₂ , R ₁₂ , G ₁ , G ₂ , G ₃ , G ₄ and G ₅ are defined in Table 4) 118 compounds (which are as described above) are disclosed.

  The compounds of the formula I according to the invention are active ingredients that are prophylactically and / or therapeutically beneficial in the field of pest control even at low application rates, which have a very favorable biocidal spectrum, It is well tolerated by blood species, fish and plants. The active ingredient according to the present invention acts not only on normally susceptible animal pests, such as insects or representatives of the order Acarina, but also on all or individual developmental stages of resistant animal pests To do. The insecticidal or acaricidal activity of the active ingredient according to the invention is reduced directly, i.e. as soon as some time has elapsed, e.g. as pest destruction occurring during molting or indirectly, e.g. Occasional manifestations as egg-laying and / or hatching rates, good activity corresponds to a destruction rate (lethal rate) of at least 50-60%.

Examples of the above animal pests are:
From the order of the Acarina, for example, Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, mma sp. , Genus Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp. Dermatossus gallinae, Dermatophagoides agoides spp), Eotetranichus spp, Eriophys spp., Hemitarsonemus spp, Olympus sp. Orithodoros spp., Polyphagotarsone latus, Panonychus spp., Phylocoptrosa olneus, Phytophymone sp. s spp), Psoroptes spp., Rhipicphalus spp., Rhizoglyhus spp., Sarcoptes spp. Tarsonemus spp.) And Tetranychus spp .;
From the order of the Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp.
From the order of the Coleoptera, for example, Agriotes spp., Amphimalon majale, Anomalas orienta sp. (Astylus atomiculatus), Athenius spp, Atomalia linearis, Chaetocnema tibialis, Genus Cerotosp. spp.), Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp. ab, Diabrotica spp. , Epilacuna spp., Eremnus spp., Heteronychus arter, Hypothenemus hamlipei, Lagria lars ham, Lissohoptrus spp., Liogenys spp, Maecolas spis sp .), Myocrous armatus, Oricaephilus spp., Otiorhynchus spp., Phyllophaga sp., P. pylus sp. ), Psylliodes spp., Rhysomatus abutilis, Rhizopertha spp., S. aphididae, sp. (Somaticus spp), Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spg.
From the order of the Diptera, for example, Aedes spp., Anopheles spp, Anteregona soccata, Bactrocea oleia, Bio horsius (Bradysia spp), black fly (Calliphora erythrocephala), Ceratitis spp., Chrysomyia spp., Culex spp., Ctereb spp. , Delia spp, Drosophila m lanogaster, Fannia spp., Gastrophilus spp., Geomiza tripuncta, sp. p. .), Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestru spp., Oestru spp. , Oscinella frit, Pegomii hyoscami), Horbia spp., Ragoletis spp, Liberia quadrifaciata (S), Scatella sp. (S), Scatella sp. , Tabanas spp., Tania spp. And Tipula spp .;
From the order of the Hemoptera, for example, Acanthocolis scabrator, Acrosternum spp, Adelphocoris lineolatus, Abricota line, thalassina, Blissus spp, Chimex spp., Claviglala tomentosicollis, Creontiades spp, Distantiella theo dia. Kerpus flucatus, Dysdercus spp., Edessa spp, eustus spp., H. urs. ), Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murganti memtomirotom ), Tobacco insects (Nesidiocoris tenuis), Nezara spp., Nyius simulans, Oebalus insulazo, Piesma psp. Genus (Rhodnius spp.), Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp., Santinopha spp. ), Vatiga ildenns;
Ashirutoshiumu-Pisumu (Acyrthosium pisum), Adarugesu genus (Adalges spp), Agariana-Enshigera (Agalliana ensigera), Agonosena-Tarugionii (Agonoscena targionii), Areurojikusu genus (Aleurodicus spp), Areurokantsusu genus (Aleurocanthus spp), Areurorobusu-Barodenshisu (Aleurolobus barodensis, Aleurothrixus floccusus, Areyrodes brassicae, Amarasca bituttula, Amritos atkinsoni us atkinsoni), Anonydiella spp., Aphididae, Aphis spp., Aspidiotus spp., Acotoracer sera. , Bemisia spp, Brachycaudus spp, Breconcoryne brassicae, Capposylla spp, Carrotella sp. Cavalipa sp. ), Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicella spp, Cofida spp, Cofapect Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia (Diuris isp) Poasuka genus (Empoasca spp. ), Apple beetle (Eriosoma larigerum), erythroneuura spp., Genus Gascardia spp., Genus spr. ), Hyperomyzus pallidus, Idioscopus cyperalis, Jacobiasca lybica, Laodelfaxum L. corni), Lepidosaphes spp., Poppy aphid (Lopaphis erysimi), Lyogenys maidis (Macrophum spp.), Maphanarph spp. Mepolophium dirhodum, Myndus crudus, Myzus spp., Neoxoptera sp, genus Nepalp. Ooa Buramushi (Nippolachnus piri Mats), Odonasupisu-Rutae (Odonaspis ruthae), Oreguma-Ranigera-presenters (Oregma lanigera Zehnter), bayberry whitefly (Parabemisia myricae), Paratorioza-Kokkereri (Paratrioza cockerelli), Paruratoria genus (Parlatoria spp.), Pemufigusu Genus (Pemphigus spp.), Corn planthopper (Peregrinus maidis), Perkinsiella spp. (Phordon humuli), phylloxera spp (Phloxera spp) spp. ), Pseudaulacaspis spp., Pseudococcus spp., Pseudomoscelis seriatus, Psylla spp., Psylla spp. Quadraspidiiotus spp.), Quesada gigas, Recilia dorsalis, Rhoparosifum spp., Saisettia spde. ) Shitobion genus (Sitobion spp.), Sejirounka (Sogatella furcifera), Supishisuchirusu-Fesuchinusu (Spissistilus festinus), Tarofagasu - Proserpine (Tarophagus Proserpina), Tokisoputera genus (Toxoptera spp), Toriareurodesu genus (Trialeurodes spp), Torijisukasu-Suporobori (Tridiscus sporoboli ), Trionymus spp, Triza erytreae, Unaspis citri, Zygina flammigera, Zyginia stigra cutellaris);
From the order of the Hymenoptera, for example, Acromymex, Arge spp, Atchia spp., Cephus spp., Diprion spp. (Diplionidae), Giantia bee (Gilpinia polytoma), Hoplocampa spp., Kearis (Lasius spp.), Yeohimeri (Momomori haraonis), Nediprion (p. Invicta (Slenopsis invicta), Solenopsis genus (Solenopsis s . P) and Vespa spp (Vespa spp).;
From the order of the Isoptera, for example, Coptothermes spp, Corniternes cumulans, Incitermes spp, Macrotermes spes, Masterm sp. Microtermes spp., Reticulitermes spp .; Solenopsis geminate
From the order of the Lepidoptera, for example, Acrylis spp., Adoxophys spp., Aegeria spp., Agrotis spp., Alabama algae Algae algae Genus (Amylois spp.), Anticalcia gemmatalis, Archhips spp., Argyrestia spp., Argylotaenia spp. Ratricus thuleberiera (Bucculatrix thurb riella, African swim, Cadra cautella, Carposina nipponensis, Chilo spp., Chiristo spia, Choristonia sp. ambiguella), Cnaphalocrossis spp., Cnephasia spp., Cochiris spp., Coleophora spp., Coliophora sp. ila flava), Crambus spp, Crocidomia binnotalis, Cryptophlevia leucotia, Spidalima perspitalis (Cydaliperp) (Diaphania perspecialis), Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina (Eldana saccharina) ), Epinotia spp, Estigmene acrea, Etiella zinkkinella, Eucosma spp., Eupoecilia sp. Genus (Euxoa spp.), Feltia jaculiferia, Graphorita spp., Hedia nuiferana, Heliotis spl., Heithis spl. (Herpetogram a spp), the United States white Arctiidae (Hyphantria cunea), Kei Feria Rikoperushisera (Keiferia lycopersicella), sorghum moth (Lasmopalpus lignosellus), Reukoputera-Shitera (Leucoptera scitella), Ritokorechisu genus (Lithocollethis spp.), Hosobahimehamaki (Lobesia botrana), Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra megass (Mamestra megasas) ca sexta), Mythimna spp, Noctua spp, Operoftera spp., Orniodes indica (Ostribe genus). (Pandemis spp.), Pinelis flammea, Papaipema nebris, Peptinophora gossiipela, Coffee leafhopper (Perileucopter pulp) horimaea operculella), cabbage butterfly (Pieris rapae), Pierisu genus (Pieris spp. ), Plutella xylostella, Place spp., Pseudoplusia spp, Rachiplusia nu, Richia albicopa sp., Richia albicopa sp. (Sesamia spp.), Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp. Tortrix spp.), Iraqusaginawaba (T Richioplusia ni), Tomato absoluta, and Yponomeuta spp .;
From the order of the Mallophaga, for example, Damalinea spp. And Trichodictes spp .;
From the order of the Orthoptera, for example, the cockroach genus (Blatta spp.), The German cockroach genus (Blattella spp.), The genus (Glylottalpa spp.), The genus cockroach (Leucophaea maderae), the genus sp. -Hexaductila (Necurtilla hexadactyla), Cockroach spp., Scapteriscus spp., And Cristocerca spp .;
From the order of the Psocoptera, for example, Liposcelis spp .;
From the order of the Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. And Xenopsilla cheopes;
From the order of the Thysanoptera, for example, Calliotrips phaseoli, Franchiniella spp., Heliotrips spp, Helsintrips sp., Helsintrips sp. Scitotrips aurantii, Soybean thrips (Sericotrips variabilis), Taeniotrips spp., Thrips spp;
From the order of the Thysanura, for example, Lepisma saccharina.

  The active ingredients according to the present invention are especially those mentioned above which occur in plants, especially useful plants and ornamental plants in agriculture, horticulture and forests, or organs such as fruits, flowers, leaves, stems, tubers or roots of such plants. It can be used to control, i.e. control or destroy, types of pests, and in some cases even plant organs formed at a later time remain protected from these pests.

  Suitable target crops are in particular grains such as wheat, barley, rye, oats, rice, corn or sorghum; beets such as sugar beets or feed beets; fruits such as apples, pears, plums, peaches, almonds, cherries Or berries, for example, berries, nuclear fruits or soft fruits such as strawberries, raspberries or blackberries; legumes such as kidney beans, lentils, peas or soybeans; rapeseed, mustard, poppy, olives, sunflower, palm Oil and fat crops such as castor, cacao or ground nut; cucurbits such as pumpkin, cucumber or melon; fiber plants such as cotton, flax, hemp or jute; citrus fruits such as orange, lemon, grapefruit or tangerine Fruit; spinach Vegetables such as lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes or peppers; Lauraceae plants such as avocado, cinnamon or camphor; and also tobacco, nuts, coffee, eggplant, sugar cane, Tea, pepper, grapes, hops, plantains, latex plants and ornamental plants.

  The active ingredients according to the present invention include bean aphids (Aphis craccivora), diabrotica balteata, heliothis virescens, peaches aphids (Myzes aphids) in cotton, vegetables, corn, rice and soybean crops. It is particularly suitable for controlling moths (Plutella xylostella) and Spodoptera littoralis. The active ingredient according to the present invention is further comprised of the genus Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), and Emposka (preferably in vegetables and vineyards). It is particularly suitable for controlling Lepinotarsa (preferably in potatoes) and Chilo supressalis (preferably in rice).

  In a further aspect, the present invention relates to plant parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular, root-knot nematodes, foxtail nematodes (Meloidogyne hapla), melodyogyne incognita, (Meloidyne javanica), Alenaria root-knot nematode (Meloidogyne arenaria) and other Meloidogyne genus (Meloidone) species; cyst-forming nematode; , Soybean cyst nematode ( eterodera glycines), sugar beet nematode (Heterodera schachtii), clovercyst nematode (Heterodera trifolii), and other heterodera (Heterodera) species; (Aphelenchoides) species; Sting nematode, Belonolimus longicaudatus and other Belonolimus species; pine nematode, ph. Bursaphelenchus species; Ring nematode, Criconema species, Criconemella species, Criconemoides species, Mesocrimones and Mesocricene species; Destructor, Nylenchus dipsici, and other Ditylenchus species; Awl nematode, Dolichodorus species; Spiral nematodes Liocotylenchus multiincinctus and other Helicotyrenchus species; Syathe and Sheathoid nematode; Hirshmanniella species; Lance nematode, Hoploaimus species; Niseko nematode, Nacobus species; Needle nematode, Longidus elon atus Longidorus spp .; Pin nematode, Pratylenchus spp. curvitatus), Platylenchus goodeyi and other Pratylenchus species; Burrowing nematode, Banana negroglis and other species of Radophorus similis Genus Radophorus; Reniform nematode, Rotilenchus robustus, Rotyrenchus reniformis and other Rotyn genus S (Stubby root nematode), Trichodorus primitibus and other Trichodorus species, Paratrichodorus species; orhynchus craytoni), Tylencorhynchus dubius, and other Tylenchorinxus species; Citrus nematode, Tyrenchurus Plant parasitic nematodes such as Xifinema species; and Subangina spp. ), Hyspoperine spp., Macroposthonia spp., Melinius spp., Punctodella spp., And other quinus lucius sp. It also relates to a method for controlling damage to plants and plant parts by nematode species.

  The compounds of the present invention may also have activity against mollusks. Examples of molluscs include, for example, Ampullariidae; Arion (A. atter, A. circcumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. hortensis) ); Ochlodina; Deroceras (D. agrestis, D. Empiricorum ( Empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatas); Euumphalia; (Galba) (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae Helicigona albustorum )); Helicodiscus; Helix (H. aperta); Limax (L. Cineleoni) L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellas); Lymnacea; Milax (M.gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. acatic) )); And the genus Vallonia and Zanitoides.

  The term “crop” is recombinant so that it is possible to synthesize one or more selectively acting toxins as known, for example, from toxin-producing bacteria, in particular Bacillus bacteria. It should be understood to include crops transformed by the use of DNA technology.

  Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins derived from Bacillus cereus or Bacillus popillie; or δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa, Insecticidal proteins derived from Bacillus thuringiensis, such as Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A; or bacterial colony forming nematodes For example, Photolabdas luminescens, Xenolab Insecticidal proteins of Photorhabdus spp., Such as Xenorhabdus nematofilus; Xenorhabdus spp .; neurotoxins such as scorpion toxins, spider toxins, bee toxins and other insects Toxins produced by animals; toxins produced by fungi, such as Streptomyces toxins, plant lectins, such as pea lectin, barley lectin or yukinohana lectin; agglutinin; trypsin inhibitor, serine protease inhibition Agents, proteinase inhibitors such as patatin, cystatin, papain inhibitors; ribosomes such as lysine, corn-RIP, abrin, ruffin, saporin or bryodin Inactivated protein (RIP); 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitor, steroid metabolizing enzymes such as HMG-COA-reductase, sodium channel or calcium channel Examples include ion channel blockers such as blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

  In the context of the present invention, δ-endotoxin is, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or a plant insecticidal protein (Vip), eg Vip1, Vip2, Vip3 or Vip3A, It is understood by toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by new combinations of different domains of these proteins (see, eg, WO 02/15701). Cleaved toxins such as cleaved Cry1Ab are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such an amino acid substitution, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (WO 03/053). (See pamphlet No. 018810).

  Examples of such toxins or transgenic plants capable of synthesizing such toxins are described, for example, in European Patent Application Publication No. A0374753, International Publication No. WO 93/07278, International Publication No. WO 95/34656. No. pamphlet, European Patent Application Publication No. A0427529, European Patent Application Publication No. A451878 and International Publication No. 03/052073.

  Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. CryI-type deoxyribonucleic acids and their preparation are described, for example, in WO 95/34656, EP-A 0367474, EP-A 0197979 and WO 90/13651. Is known.

  The toxins contained in the transgenic plants confer resistance to the pests. Such insects are found in insect taxonomic groups, but are particularly common in beetles (Coleoptera), Diptera (Diptera) and moths (Lepidoptera). It is done.

  Transgenic plants that contain one or more genes encoding insecticidal resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are YieldGard® (a corn variety that expresses Cry1Ab toxin); YieldGard Rootworm® (a corn variety that expresses Cry3Bb1 toxin); YieldGard Plus® (Cry1Ab and Cry3Bb1 toxins) Corn varieties); Starlink® (corn varieties expressing Cry9C toxin); Herculex I® (Cry1Fa2 toxin, and the enzyme phosphinotricin N-acetyl to obtain resistance to the glufosinate ammonium herbicide Corn varieties expressing transferase (PAT); NuCOTN 33B® (cotton varieties expressing Cry1Ac toxin); Bollga dI® (cotton varieties expressing Cry1Ac toxin); Bollgard II® (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot® (cotton varieties expressing Cip1A and Cry1Ab toxins) NewLeaf® (potato variety expressing Cry3A toxin); NatureGuard®, Agrisure® GT Advantage (GA21 glyphosate resistant trait), Agurisure® CB Advantage trait (Bt11C Awanome trait) ) And Protecta (registered trademark).

Further examples of such transgenic crops are as follows:
1. Bt11 corn from Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96/05/10. Genetically engineered maize conferred resistance to attack by European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 corn also expresses the enzyme PAT by genetic engineering in order to gain resistance to the herbicide glufosinate ammonium.

2. Bt176 corn from Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96/05/10. Genetically modified maize conferred resistance to attack by European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of Cry1Ab toxin. Bt176 maize also expresses the enzyme PAT by genetic engineering in order to gain resistance to the herbicide glufosinate ammonium.

3. MIR604 maize from Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96/05/10. Corn made insect resistant by transgenic expression of the modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03/018810.

4). Monsanto Europe S. A. MON 863 corn, registration number C / DE / 02/9, manufactured by (270-272 Avenue de Turbanen, B-1150 Brussels, Belgium). MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

5. Monsanto Europe S. A. IPC 531 cotton manufactured by (270-272 Avenue de Turbanen, B-1150 Brussels, Belgium), registration number C / ES / 96/02.

6). 1507 corn from Pioneer Overseas Corporation (Avenue Tesco, 7 B-1160 Brussels, Belgium), registration number C / NL / 00/10. Genetically modified maize for expression of the PAT protein to obtain resistance to the protein Cry1F and the herbicide glufosinate ammonium to obtain resistance to certain Lepidoptera insects.

7). Monsanto Europe S. A. NK603 × MON 810 corn, registration number C / GB / 02 / M3 / 03, manufactured by (270-272 Avenue de Türren, B-1150 Brussels, Belgium). It consists of hybrid corn varieties bred by conventional methods by crossing genetically modified varieties NK603 and MON810. NK603 × MON 810 corn is a protein CP4 EPSPS obtained from Agrobacterium sp. Strain CP4 that confers resistance to the herbicide Roundup® (containing glyphosate), and certain species including European corn borer The Cry1Ab toxin obtained from Bacillus thuringiensis subsp. Kurstaki, which provides resistance to Lepidoptera, is also expressed by genetic recombination.

  Transgenic crops of insect-tolerant plants are also described in BATS (Zentrum fuerheitund Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).

  The term “crop” means, for example, an antipathogenic substance having a selective action, such as a so-called “pathogenicity-related protein” (PRP, eg see EP-A-0392225). It should also be understood to include crops transformed by use of recombinant DNA technology so that can be synthesized. Examples of such anti-pathogenic substances and transgenic plants capable of synthesizing such anti-pathogenic substances are described, for example, in EP-A-0 392 225, WO 95/33818. It is known from the pamphlet and from EP-A 0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

  Anti-pathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers such as sodium channel or calcium channel blockers, eg, viral KP1, KP4 or KP6 toxins; stilbene synthase; bibenzyl Synthase; chitinase; glucanase; so-called “pathogenicity related proteins” (PRP; see, for example, EP-A-0392225); anti-pathogenic substances produced by microorganisms, eg peptide antibiotics or heterocyclics Antibiotics (see, for example, WO 95/33818) or proteins or polypeptide factors involved in plant pathogen defense (so-called “plant disease resistance genes described in WO 03/000906”) " And the like.

  Further areas of use of the compositions according to the invention include the protection of storage goods and storage rooms and raw materials (such as wood and textiles), the protection of floor coverings and buildings, and the hygiene field, in particular pests of the type described above. Protection of humans, livestock and productive livestock from

  The present invention also provides methods for controlling pests (such as mosquitoes and other pathogens; see also http://www.who.int/malaria/vector_control/irs/en/). In one embodiment, a method for controlling pests comprises brushing, roller coating, spraying, coating or dipping a composition of the invention on a target pest, on its habitat, or on a surface or substrate. The step of applying is included. As an example, IRS (indoor residual spray) application of surfaces such as walls, ceilings or floors is envisaged by the method of the present invention. In another embodiment, it is envisaged that such a composition is applied to a substrate, such as a nonwoven or fabric material in the form of a net, garment, bedding, curtain and tent (or a form that can be used to make them). Has been.

  In one embodiment, a method for controlling such pests comprises a pesticidally effective amount of a composition of the invention so as to provide effective residual pest control activity to the surface or substrate. Applying an object to a target pest, to its habitat, or to a surface or substrate. Such application can be performed by brush application, roller application, spraying, application or dipping of the pesticidal composition of the present invention. By way of example, IRS application on a surface such as a wall, ceiling or floor surface is envisioned by the method of the present invention to provide the surface with effective residual pest control activity. In another embodiment, such compositions for pest persistence control in substrates such as fabric materials in the form of nets, clothing, bedding, curtains and tents (or forms that can be used in their manufacture). It is assumed to be applied.

  Substrates comprising nonwovens, fabrics or nets to be treated can be made of natural fibers such as cotton, raffia, jute, flax, sisal, linen or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile. . Polyester is particularly preferred. The method of textile processing is, for example, International Publication No. 2008/151984 pamphlet, International Publication No. 2003/034823 pamphlet, US Pat. No. 5,613,072, International Publication No. 2005/64072 pamphlet, International Publication No. 2006/128870. It is known from the pamphlet, EP 1724392, WO2005113886 or WO2007 / 090739.

  A further field of use of the composition according to the invention is in the field of trunk injection / stem treatment of all ornamental trees and all kinds of fruit trees and nuts.

In the field of stem injection / stem treatment, the compounds according to the invention are particularly suitable for the above-mentioned Lepidoptera and Coleoptera wood-boring insects, as shown in Table A and Particularly suitable for the wood-perforating insects listed in B.
Table A. Examples of economically important exotic wood-piercing insects

Table B. Examples of economically important native wood-piercing insects

  The present invention also includes, for example, beetles, caterpillars, fire ants, ground pears, ground pears, ground beetles, mites, scales, scale insects, mealybugs, ticks, leaf beetles, southern chinch bugs and earthworms. It can be used to control any insect pest that may be present in turfgrass. The present invention can be used to control insect pests at various stages of the life cycle, including eggs, larvae, nymphs and adults.

  In particular, the present invention relates to earthworms (Cyclocephala spp. (Eg, masked chafer, C. lurida), Rhizotrogus spp. (Eg, European Rhesus spp.)). R. majalis), Cotinus spp. (Eg, C. nitida), Popilia spp. (Eg, Japan beetle), P. japonica)), Phyllophaga spp. (Eg, May / June beetle), Athenius spp. (E.g., Black turfgrass atenaius, A. spretus), Maladera spp. (E.g., M. castanea, M. castanea) and Tomalus Genus (Tomarus spp.), Cotton beetle (Margarodes spp.), Kera (towny, Southern), and short-cage types; Scapteriscus spp. (Gryllotalpa africana) and leather jacket (European crane f y), crane fly genus (Tipula spp.)) including, may be used to control insects pests lawn grass roots bait.

  The present invention also includes the beetles (Spodoptera frugiperda), and the common armyworm (Pseudaletia unipunta, etc.), the genus S. Weevil (such as S. ventus verstitus) and S. parvulus, and sod webworms (Crambus spp.) And tropical sod webworms, (Herpetogramma phaeoperalis, etc.) No, it may be used to control grass insect pests living in the straw.

  The present invention also relates to the mite (Eriophys cynodonodisigashirasigashirasigasushisushienshigashi), the tick (Eriophysus cynodonodisigashirasigashigashigashigashigashigashi), the ticks of Bermudagrass (Eryophyces cynodonodishirasigasushienshigashigashigashigashigashigashigashigashigashigashigashigashi). Scales of scales (Antonina graminis), two-lined spotted bugs (Propsia bicinta), leafhoppers, leafworms (Nectuidae), and worms To control insect pests that feed on turfgrass leaves Can be used.

  The present invention can also be used to control other turfgrass pests, such as the red ant (Solenopsis invicta) that creates anthills on the lawn.

  In the field of hygiene, the composition according to the present invention comprises a hard tick, soft tick, scabies mite, tsutsugamushi, flies (fly flies and licking flies), parasitic fly larvae, lice, It is effective against ectoparasites such as lice, lice and fleas.

Examples of such parasites are:
Among the lice (Anoplurida): Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp.

  Among the order of the Mallophagida: Trimenopon spp., Tanpon spp., Trinoton spp., Bovicola spp., Wernekiella er ), Lepikentron spp., Damarina spp., Trichodictes spp. And Felicola spp.

  Among the Diptera and its suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp. Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomia spp., Curicoes spp. spp.), Hybomitra spp., Atylotus spp., Tabanus spp., sesame Haematopota spp., Phillipomia spp., Braula spp., Musca spp., Togesima spp. (Haematobia spp.), Morelia spp., Fannia spp., Glossina spp., Calliphora spp., Lucpih spr. spp.), Wohlfahrtia spp., Sarcoph ga spp.), Oestrus spp., Hypoderma spp., Gastrophilus spp., Hippobosca spp., Lipops spp. and Lipops spp. .).

  Among the fleas (Siphonaptida), for example, the genus Human flea (Pulex spp.), The genus Ctenocephalides spp., The genus Nenopsylla spp., And the genus Ceratophyllus spp.

  Among the Heteroptera, for example, Chimex spp., Triatoma spp., Rhodnius spp., Panstromylus spp.

  Among the cockroaches (Blattarida), for example, the cockroach (Blatta orientalis), the cockroach (Peripraneta americana), the cockroach (Blatellagermanica) and the genus Spella (Supella spp.).

  Among the tick subclasses (Acaria (Acarida)) and Tickinae (Mestatigmatata) and Mesostigmata (Merostigmatata), for example, Argas spp., Ornithodorus spp., Otobius (Tobus genus) spp.), Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp. ), Rhipicephalus spp., Dermanyssus spp., La Raillietia spp., Pneumonysus spp., Sternostoma spp. And Barroa spp.

  Among the order Actinida (Prostigmata) and Acarida (Astigmata), for example, Acarapis spp., Cheylettiella spp. Ornithocheyletia spp., Myobia spp., Psorgatesspp., Demodex spp., Limtropor spp. , Acarus spp., Tyrophagus spp., Carocarid mite (Calog) yphus spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Choroptes spp., Sp. Sarcoptes spp., Notoderes spp., Knemidocoptes spp., Cytodites spp. And Laminosoptes sp.

  The composition according to the invention is also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glue, paints, paper and cardboard, leather, floor coverings and buildings. is there.

  The composition according to the invention can be used, for example, against the following pests: Hylorupes bajulus, Chlorophorus pilosis, Anobium puncatum, Xenostobium X rufuvillosum), Petilinus specicornis, Dendrobium pertinex, Ernobius mollis, Onibira citrus, Priopitarum ctus africanus, Lyctus pnicolis, Lyctus linearis, Lyctus pylense, Troxoxyn squirrel ), Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrus bruneus, Heterobostristchurus brunerus Beetles such as Sinoxylon spec. And Dinoderus minutus, as well as Syrex juvencus, Urocerus giga, Urocerus giga urus, g ) And other species of hymenopterans, as well as Kalothermes flavicollis, Cryptothermes brevis, Heterotermes indicola, Rhizocidal ermes flavipes), Letty Kurite Rumesu-Santonenshisu (Reticulitermes santonensis), Letty Curie Tel female Rushifugusu (Reticulitermes lucifugus), Mukashishiroari (Mastotermes darwiniensis), Nevada giant termite (Zootermopsis nevadensis) and the Formosan subterranean termite (Coptotermes formosanus) termites, and the like, as well as western A stain such as a stain (Lepisma saccharina).

  Accordingly, the present invention also provides emulsions, suspension concentrates, microemulsions, oil dispersible, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, It also relates to a pesticidal composition such as a dust, a granule or an inclusion in a polymer substance, the pesticidal composition comprising at least one of the active ingredients according to the invention, intended Should be selected according to the purpose and general circumstances to be met.

  In these compositions, the active ingredient is in pure form, for example as a solid active ingredient of a specific particle size, or preferably, as a bulking agent, such as a solvent or a solid carrier, or a surface active compound (surfactant). It is used together with at least one of the adjuvants usually used in the technical field of formulation.

Examples of suitable solvents are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably xylene mixtures, C ₈ -C ₁₂ fraction alkylbenzenes, such as alkylated naphthalenes or tetrahydronaphthalene, paraffin or cyclohexane Aliphatic or cycloaliphatic hydrocarbons such as, alcohols such as ethanol, propanol or butanol, glycols and their ethers such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether and Strong polarity such as ketones such as esters, cyclohexanone, isophorone or diacetone alcohol, N-methylpyrrolid-2-one, dimethyl sulfoxide or N, N-dimethylformamide Solvent, water, non-epoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil, and epoxidized or epoxidized vegetable oils such as silicone oil.

  For example, solid carriers used in dusts and dispersible powders are generally ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. It is also possible to add highly dispersed silica or highly dispersed absorbent polymers in order to improve the physical properties.

  Suitable particulate adsorptive carriers for granules are porous types such as pumice, brick grit, buffstone or bentonite, and suitable non-absorbent carrier materials are calcite or sand. . In addition, many inorganic or organic particulate materials can be used, in particular dolomite or ground plant residues.

  Suitable surface-active compounds are nonionic, cationic and / or anionic surfactants or surfactant mixtures with good emulsifying, dispersing and wetting properties, depending on the type of active ingredient to be formulated. The surfactants described below are only considered as examples; many additional surfactants commonly used in the art of formulation and suitable according to the present invention are described in the relevant literature.

  Suitable nonionic surfactants are in particular polyglycol ether derivatives of aliphatic or alicyclic alcohols, polyglycol ether derivatives of saturated or unsaturated fatty acids, or polyglycol ether derivatives of alkylphenols, which are about May contain from 3 to about 30 glycol ether groups and from about 8 to about 20 carbon atoms in the (cyclic) aliphatic hydrocarbon group, or from about 6 to about 18 carbon atoms in the alkyl portion of the alkylphenol Can do. Polypropylene glycol, ethylenediaminopolypropylene glycol or alkylpolypropylene glycol having from 1 to about 10 carbon atoms and from about 20 to about 250 ethylene glycol ether groups and from about 10 to about 100 propylene glycol ether groups in the alkyl chain Also suitable are water-soluble polyethylene oxide adducts. Typically, the above compounds contain 1 to about 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxy polyethoxyethanol, castor oil polyglycol ether, polypropylene glycol / polyethylene oxide adduct, tributylphenoxy polyethoxyethanol, polyethylene glycol or octylphenoxy polyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.

  Cationic surfactants in particular have at least one alkyl group with about 8 to about 22 C atoms as substituents and lower alkyl or hydroxyalkyl or benzyl groups as further substituents (non-halogenated or halogenated). It is a quaternary ammonium salt generally possessed. The salt is preferably in the form of a halide, methyl sulfate or ethyl sulfate. Examples are stearyltrimethylammonium chloride and benzylbis (2-chloroethyl) ethylammonium bromide.

  Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds. Examples of suitable soaps are those of fatty acids having from about 10 to about 22 C atoms, such as oleic acid or stearic acid, or sodium or potassium salts of natural fatty acid mixtures obtained, for example, from coconut oil or tall oil. Alkali metal salts, alkaline earth metal salts or (unsubstituted or substituted) ammonium salts; fatty acid methyl taurates should also be mentioned. However, synthetic surfactants, in particular aliphatic sulfonates, aliphatic sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates are used more frequently. In general, aliphatic sulfonates and aliphatic sulfates exist as alkali metal salts, alkaline earth metal salts or (substituted or unsubstituted) ammonium salts and generally have an alkyl group of about 8 to about 22 C atoms. , Alkyl should also be understood to include the alkyl portion of the acyl group; examples of which include lignosulfonic acid, dodecyl sulfate or fatty alcohol sulfate mixtures prepared from natural fatty acids. Sodium salt or calcium salt. This group also includes sulfates of aliphatic alcohol / ethylene oxide adducts and salts of sulfonic acids. The sulfonated benzimidazole derivative preferably contains two sulfonyl groups and a fatty acid group of about 8 to about 22 C atoms. Examples of alkylaryl sulfonates are the sodium, calcium or triethanolammonium salts of decylbenzene sulfonic acid, of dibutyl naphthalene sulfonic acid or of naphthalene sulfonic acid / formaldehyde condensate. In addition, suitable phosphates such as p-nonylphenol / (4-14) ethylene oxide adduct phosphates or phospholipid salts are also possible.

  In general, the composition comprises from 0.1 to 99%, in particular from 0.1 to 95% active ingredient and from 1 to 99.9%, in particular from 5 to 99.9% of at least one solid or liquid adjuvant. In general, 0 to 25%, especially 0.1 to 20% of the composition can be surfactants (% means weight percent each). Although concentrated compositions tend to be preferred as commercial products, the end consumer generally uses dilute compositions with a fairly low concentration of active ingredient.

  Typically, the premix formulation for foliar application is 0.1-99.9%, especially 1-95% of the desired ingredients, and 99.9-0.1%, especially 99-5. % Of a solid or liquid adjuvant (including, for example, a solvent such as water), the adjuvant being a surfactant in an amount of 0-50%, especially 0.5-40%, based on the premix formulation It can be an agent.

  Typically, tank mix formulations for seed treatment application are 0.25-80%, especially 1-75% of the desired ingredients, and 99.75-20%, especially 99-25% of solid or liquid aids. Agent (including, for example, a solvent such as water), and the adjuvant may be a surfactant in an amount of 0-40%, especially 0.5-30%, based on the tank mix formulation.

  Typically, the premix formulation for seed treatment application is 0.5-99.9%, especially 1-95% of the desired ingredients, and 99.5-0.1%, especially 99-5. % Of a solid or liquid adjuvant (including, for example, a solvent such as water), the adjuvant being a surfactant in an amount of 0-50%, especially 0.5-40%, based on the premix formulation It can be an agent.

  Commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), but end users typically use dilute formulations (eg, tank mix compositions). Will.

  A preferred seed treatment premix formulation is an aqueous suspension concentrate. The formulation can be applied to the seed using conventional processing techniques and machinery, such as fluid bed technology, roller milling, rotostatic seed treaters, and drum coaters. Other methods such as a spouted bed may also be useful. Seeds can be pre-classified prior to application. After application, the seeds are typically dried and then transferred to a classifier for classification. Such procedures are well known in the art.

  In general, the premix composition of the present invention comprises from 0.5 to 99.9, in particular from 1 to 95, preferably from 1 to 50% by weight of the desired components, and from 99.5 to 0.1, in particular Containing 99-5% by weight of solid or liquid adjuvant (e.g. including a solvent such as water) and the adjuvant (or adjuvant) is 0-50, in particular, based on the weight of the premix formulation, It may be a surfactant in an amount of 0.5-40% by weight.

Examples of foliage formulation types for premix compositions are as follows:
GR: granule WP: wettable powder WG: hydratable granule (powder)
SG: water-soluble granules SL: soluble concentrate EC: emulsifiable concentrate EW: oil-in-water emulsion ME: microemulsion SC: aqueous suspension concentrate CS: aqueous capsule suspension OD: oil-based suspension concentrate, And SE: aqueous supo-emulsion.

On the other hand, examples of seed treatment formulation types for premix compositions are as follows:
WS: wettable powder for seed treatment slurry LS: liquid solution for seed treatment ES: emulsion for seed treatment FS: suspension concentrate for seed treatment WG: hydrated granules, and CS: aqueous capsule suspension.

  Examples of suitable formulation types for tank-mix compositions are solutions, diluted emulsions, suspensions, or mixtures thereof, and dusts.

  A preferred composition is specifically composed as follows (% = mass percent).

emulsion:
Active ingredient: 1 to 95%, preferably 5 to 20%
Surfactant: 1-30%, preferably 10-20%
Solvent: 5-98%, preferably 70-85%

Dust agent:
Active ingredient: 0.1 to 10%, preferably 0.1 to 1%
Solid carrier: 99.9-90%, preferably 99.9-99%

Suspension concentrate:
Active ingredient: 5 to 75%, preferably 10 to 50%
Water: 94-24%, preferably 88-30%
Surfactant: 1-40%, preferably 2-30%

Wettable powder:
Active ingredient: 0.5 to 90%, preferably 1 to 80%
Surfactant: 0.5-20%, preferably 1-15%
Solid carrier: 5 to 99%, preferably 15 to 98%

Granule:
Active ingredient: 0.5-30%, preferably 3-15%
Solid carrier: 99.5-70%, preferably 97-85%

Preparation examples:
“Mp” means melting point (° C.). A free radical represents a methyl group. ¹ H NMR measurements are recorded on a Brucker 400 MHz spectrometer and chemical shifts are given in ppm relative to the TMS standard. As indicated, spectra are measured in deuterated solvents. Common abbreviations: aq = aqueous solution, min = min, h = hour, sat = saturation, R _t = retention time, mCPBA = meta-chloroperbenzoic acid, MeOH = methanol, NaHCO ₃ = sodium bicarbonate, Na ₂ CO ₃ = sodium carbonate, HCl = hydrogen chloride, NBS = N-bromosuccinimide, PdCl ₂ (dppf) = [1,1-bis (diphenylphosphino) ferrocene] dichloropalladium (II).

LCMS method:
Method 1:
SC_BASE, apparatus: Agilent 1100 binary pump: G1312A, degassing apparatus; autosampler, ColCom, DAD: Agilent G1315B, 220-320 nm, MSD: Agilent LC / MSD G6130B ESI, pos / neg 100-800; ELSD PL-ELS2100 gas Flow 1.1 ml / min, gas temperature: 50 ° C .; column: Waters XSelect ™ C18, 30 × 2.1 mm, 3.5 μ, temperature: 25 ° C., flow rate: 1 mL / min, gradient: t ₀ = 2% A, t _1.6min = 98% A, t _3min = 98% A, Posttime: 1.3 minutes, eluent A: 5% 10 mM carbonic acid in water in 95% acetonitrile + acetonitrile. Ammonium hydrogen, eluent B: 10 mM in water Ammonium hydrogen (pH = 9.5).

Method 2:
AN_BASE, apparatus: Agilent 1100 binary pump: G1312A, degassing apparatus; autosampler, ColCom, DAD: Agilent G1315B, 220-320 nm, MSD: Agilent LC / MSD G6130B ESI, pos / neg 100-800; ELSD PL-ELS2100 gas Flow 1.1 ml / min, gas temperature: 50 ° C .; column: Waters XSelect ™ C18, 50 × 2.1 mm, 3.5 μ, temperature: 25 ° C., flow rate: 0.8 mL / min, gradient: t ₀ = 2% A, t _3.5min = 98% A, t _6min = 98% A, post time: 2 minutes, eluent A: 5% 10 mM ammonium bicarbonate in water in 95% acetonitrile + acetonitrile, Eluent B: 10 mM ammonium bicarbonate in water pH = 9.5).

Method 3:
Electrospray source (polarity: positive or negative ion, capillary: 3.00 kV, cone range: 30-60 V, extraction device: 2.00 V, ion source temperature: 150 ° C., desolvation temperature: 350 ° C., cone gas flow: Waters mass spectrometer (SQD or ZQ single quadrupole mass spectrometer) equipped with 0 L / h, desolvation gas flow: 650 L / h, mass range: 100-900 Da) and Waters Acquity UPLC: binary The spectra were recorded with a pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters UPLC HSS T3, 1.8 mm, 30 × 2.1 mm, temperature: 60 ° C., DAD wavelength range (nm): 210-500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH; gradient: 0% B for 0 min, 100% A; 100% B for 2.7-3.0 min; flow rate (ml / min) 0.85.

Method 4:
Electrospray source (polarity: positive or negative ion, capillary: 3.00 kV, cone range: 30-60 V, extraction device: 2.00 V, ion source temperature: 150 ° C., desolvation temperature: 350 ° C., cone gas flow: Waters mass spectrometer (SQD, SQDII or ZQ single quadrupole mass spectrometer) equipped with 0 L / h, desolvation gas flow: 650 L / h, mass range: 100-900 Da) and Waters Acquity UPLC : Spectra were recorded with a binary pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 ° C., DAD wavelength range (nm): 210-500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH; gradient: 10-100% B in 1.2 minutes; flow rate (ml / min) 0.85.

Method 5:
The spectra were recorded on a Waters ACQUITY SQD mass spectrometer (single quadrupole mass spectrometer). Ionization method: electrospray. Polarity: positive ion. Capillary (kV) 3.00, cone (V) 20.00, extraction device (V) 3.00, ion source temperature (° C.) 150, desolvation temperature (° C.) 400, cone gas flow (L / hour) 60 Desolvation gas flow (L / hr) 700; Mass range: 100-800 Da; DAD wavelength range (nm): 210-400.
ACQUITY UPLC method from Waters with the following HPLC gradient conditions (solvent A: water / methanol 9: 1, 0.1% formic acid and solvent B: acetonitrile, 0.1% formic acid)

Time (min) A (%) B (%) Flow rate (ml / min)
0 100 0 0.75
2.5 0 100 0.75
2.8 0 100 0.75
3.0 100 0 0.75

  Column type: ACQUITY UPLC HSS T3 from Waters; column length: 30 mm; column inner diameter: 2.1 mm; particle size: 1.8 μm; temperature: 60 ° C.

メタノール（２５ｍｌ）中の３−クロロ−５−（トリフルオロメチル）ピリジン−２−カルボニトリル（４．０ｇ、１９．３７ｍｍｏｌ）の溶液に、ナトリウムメトキシド（ＭｅＯＨ中３０％（ｗ／ｗ））（０．１９２ｇ、１．０６６ｍｍｏｌ、０．２０ｍｌ、３０％）を加え、混合物を周囲温度で１８時間撹拌した。２，２−ジエトキシ−エタンアミン（２．７５ｇ、２０．６３ｍｍｏｌ、３．０ｍｌ）及び酢酸（２．３６ｇ、３９．３ｍｍｏｌ、２．２５ｍｌ）を加え、反応混合物を、３０分間にわたって還流状態で加熱した。反応混合物を周囲温度に冷まし、６ＮのＨＣｌ（水溶液）（１０ｍｌ）を加え、混合物を、３時間にわたって還流状態で加熱した。反応混合物を濃縮した。残渣に水を加え、水性混合物のｐＨを、飽和Ｎａ₂ＣＯ₃（水溶液）を用いて約９に調整した。沈殿した固体をろ過して取り除き、水で２回洗浄し、乾燥させた。粗生成物を、フラッシュカラムクロマトグラフィー（ヘプタン中０〜５０％の酢酸エチル勾配）によってシリカにおいて精製したところ、表題化合物（２．９４ｇ）が固体として得られた。ＬＣＭＳ（方法１）：２４８（Ｍ＋Ｈ）⁺，保持時間２．０３ｍｉｎ．¹Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６，ｐｐｍ）７．３１（２Ｈ），８．５２（１Ｈ），８．９５（１Ｈ），１３．０９（１Ｈ）． Example P1: Preparation of 3-ethylsulfonyl-2- [1-methyl-5- [3- (trifluoromethyl) phenyl] imidazol-2-yl] -5- (trifluoromethyl) pyridine (Compound P1):
Step 1: Preparation of 3-chloro-2- (1H-imidazol-2-yl) -5- (trifluoromethyl) pyridine

To a solution of 3-chloro-5- (trifluoromethyl) pyridine-2-carbonitrile (4.0 g, 19.37 mmol) in methanol (25 ml) was added sodium methoxide (30% in MeOH (w / w)). (0.192 g, 1.066 mmol, 0.20 ml, 30%) was added and the mixture was stirred at ambient temperature for 18 hours. 2,2-diethoxy-ethanamine (2.75 g, 20.63 mmol, 3.0 ml) and acetic acid (2.36 g, 39.3 mmol, 2.25 ml) were added and the reaction mixture was heated at reflux for 30 minutes. . The reaction mixture was cooled to ambient temperature, 6N HCl (aq) (10 ml) was added and the mixture was heated at reflux for 3 hours. The reaction mixture was concentrated. Water was added to the residue and the pH of the aqueous mixture was adjusted to about 9 using saturated Na ₂ CO ₃ (aq). The precipitated solid was removed by filtration, washed twice with water and dried. The crude product was purified on silica by flash column chromatography (0-50% ethyl acetate gradient in heptane) to give the title compound (2.94 g) as a solid. LCMS (Method 1): 248 (M + H) ⁺ , retention time 2.03 min. ¹ H-NMR (DMSO-d6, ppm) 7.31 (2H), 8.52 (1H), 8.95 (1H), 13.09 (1H).

乾燥テトラヒドロフラン（９０ｍｌ）中の３−クロロ−２−（１Ｈ−イミダゾール−２−イル）−５−（トリフルオロメチル）ピリジン（２．９ｇ、１１．７１ｍｍｏｌ）の溶液に、水素化ナトリウム（０．７０３ｇ、１７．５７ｍｍｏｌ、６０質量％）を加えた。１０分間撹拌した後、黄色の懸濁液が得られた。ヨードメタン（３．１８ｇ、２２．３９ｍｍｏｌ、１．４ｍｌ）を加え、混合物を周囲温度で１８時間撹拌した。ほぼ透明な茶色の溶液が得られた。反応混合物を水に注ぎ、塩水を加えた（水／塩水 約１／１）。水性混合物を酢酸エチルで２回抽出した。組み合わされた有機層を硫酸ナトリウム上で乾燥させ、濃縮した。粗生成物を、フラッシュカラムクロマトグラフィー（ヘプタン中１０〜５０％の酢酸エチル勾配）によってシリカにおいて精製したところ、表題化合物（２．７５ｇ）が油として得られた。ＬＣＭＳ（方法１）：２６２（Ｍ＋Ｈ）⁺，保持時間１．９４ｍｉｎ．¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ｐｐｍ）３．８５（３Ｈ），７．０６（１Ｈ），７．２６（１Ｈ），８．０９（１Ｈ），８．８２（１Ｈ）． Step 2: Preparation of 3-chloro-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine

To a solution of 3-chloro-2- (1H-imidazol-2-yl) -5- (trifluoromethyl) pyridine (2.9 g, 11.71 mmol) in dry tetrahydrofuran (90 ml) was added sodium hydride (0. 703 g, 17.57 mmol, 60% by weight). After stirring for 10 minutes, a yellow suspension was obtained. Iodomethane (3.18 g, 22.39 mmol, 1.4 ml) was added and the mixture was stirred at ambient temperature for 18 hours. An almost clear brown solution was obtained. The reaction mixture was poured into water and brine was added (water / brine about 1/1). The aqueous mixture was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The crude product was purified on silica by flash column chromatography (10-50% ethyl acetate gradient in heptane) to give the title compound (2.75 g) as an oil. LCMS (Method 1): 262 (M + H) ⁺ , retention time 1.94 min. ¹ H-NMR (CDCl ₃ , ppm) 3.85 (3H), 7.06 (1H), 7.26 (1H), 8.09 (1H), 8.82 (1H).

乾燥Ｎ，Ｎ−ジメチルホルムアミド（２０ｍｌ）中の３−クロロ−２−（１−メチルイミダゾール−２−イル）−５−（トリフルオロメチル）ピリジン（２．７５ｇ、１０．５１ｍｍｏｌ）の溶液に、ナトリウムエタンチオラート（１．０６１ｇ、１２．６１ｍｍｏｌ）を加え、混合物を周囲温度で１時間撹拌した。反応混合物を水／塩水（１／１）に注ぎ、水性混合物を酢酸エチルで抽出した。有機層を、水／塩水（１／１）で２回洗浄し、硫酸ナトリウム上で乾燥させ、濃縮した。残渣を、フラッシュカラムクロマトグラフィー（ヘプタン中５〜５０％の酢酸エチル勾配）によってシリカにおいて精製したところ、表題化合物（２．６７ｇ）が固体として得られた（融点８７〜８８℃）。ＬＣＭＳ（方法２）：２８８（Ｍ＋Ｈ）⁺，保持時間３．３５ｍｉｎ．¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ｐｐｍ）１．４０（３Ｈ），２．９６（２Ｈ），３．９３（３Ｈ），７．０３（１Ｈ），７．２６（１Ｈ），７．７９（１Ｈ），８．６０（１Ｈ）． Step 3: Preparation of 3-ethylsulfanyl-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine

To a solution of 3-chloro-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine (2.75 g, 10.51 mmol) in dry N, N-dimethylformamide (20 ml), Sodium ethanethiolate (1.061 g, 12.61 mmol) was added and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into water / brine (1/1) and the aqueous mixture was extracted with ethyl acetate. The organic layer was washed twice with water / brine (1/1), dried over sodium sulfate and concentrated. The residue was purified on silica by flash column chromatography (5-50% ethyl acetate gradient in heptane) to give the title compound (2.67 g) as a solid (mp 87-88 ° C.). LCMS (Method 2): 288 (M + H) ⁺ , retention time 3.35 min. ¹ H-NMR (CDCl ₃ , ppm) 1.40 (3H), 2.96 (2H), 3.93 (3H), 7.03 (1H), 7.26 (1H), 7.79 (1H ), 8.60 (1H).

ジクロロメタン（８０ｍｌ）中の３−エチルスルファニル−２−（１−メチルイミダゾール−２−イル）−５−（トリフルオロメチル）ピリジン（２．６７ｇ、９．２９ｍｍｏｌ）の溶液に、ｍＣＰＢＡ（水中７０質量％）（６．２９ｇ、２５．５ｍｍｏｌ、７０％）を一度に加えた。混合物を周囲温度で４時間撹拌した。反応混合物をジクロロメタンで希釈し、飽和チオ硫酸ナトリウム水溶液／飽和ＮａＨＣＯ₃（１／１）、飽和ＮａＨＣＯ₃で洗浄し、硫酸ナトリウム上で乾燥させ、濃縮した。残渣を、フラッシュカラムクロマトグラフィー（ヘプタン中１０〜７５％の酢酸エチル勾配）によってシリカにおいて精製したところ、表題化合物（２．４８ｇ）が固体として得られた（融点１４９〜１５０℃）。ＬＣＭＳ（方法２）：３２０（Ｍ＋Ｈ）⁺，保持時間３．１０ｍｉｎ．¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ｐｐｍ）１．３７（３Ｈ），３．７７（３Ｈ），４．０５（２Ｈ），７．０９（１Ｈ），７．１８（１Ｈ），８．７１（１Ｈ），９．１１（１Ｈ）． Step 4: Preparation of 3-ethylsulfonyl-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine

To a solution of 3-ethylsulfanyl-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine (2.67 g, 9.29 mmol) in dichloromethane (80 ml) was added mCPBA (70 mass in water). %) (6.29 g, 25.5 mmol, 70%) was added in one portion. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium thiosulfate / saturated NaHCO ₃ (1/1), saturated NaHCO ₃ , dried over sodium sulfate and concentrated. The residue was purified on silica by flash column chromatography (10-75% ethyl acetate gradient in heptane) to give the title compound (2.48 g) as a solid (mp 149-150 ° C.). LCMS (Method 2): 320 (M + H) ⁺ , retention time 3.10 min. ¹ H-NMR (CDCl ₃ , ppm) 1.37 (3H), 3.77 (3H), 4.05 (2H), 7.09 (1H), 7.18 (1H), 8.71 (1H ), 9.11 (1H).

クロロホルム（１０ｍｌ）中の３−エチルスルホニル−２−（１−メチルイミダゾール−２−イル）−５−（トリフルオロメチル）ピリジン（３１９ｍｇ、０．９９９ｍｍｏｌ）の溶液に、ＮＢＳ（１９０ｍｇ、１．０６８ｍｍｏｌ）を加え、混合物を、６０℃（油浴温度）で１時間加熱した。反応混合物を濃縮し、残渣を、フラッシュカラムクロマトグラフィー（ヘプタン中５〜４０％の酢酸エチル勾配）によってシリカにおいて精製したところ、表題化合物（２９０ｍｇ）が固体として得られた。ＬＣＭＳ（方法１）：３９８／４００（Ｍ＋Ｈ）⁺，保持時間２．１７ｍｉｎ．¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ｐｐｍ）１．３８（３Ｈ），３．７０（３Ｈ），３．９９（２Ｈ），７．１８（１Ｈ），８．７１（１Ｈ），９．２０（１Ｈ）． Step 5: Preparation of 2- (5-bromo-1-methyl-imidazol-2-yl) -3-ethylsulfonyl-5- (trifluoromethyl) pyridine

To a solution of 3-ethylsulfonyl-2- (1-methylimidazol-2-yl) -5- (trifluoromethyl) pyridine (319 mg, 0.999 mmol) in chloroform (10 ml) was added NBS (190 mg, 1.068 mmol). ) And the mixture was heated at 60 ° C. (oil bath temperature) for 1 hour. The reaction mixture was concentrated and the residue was purified on silica by flash column chromatography (5-40% ethyl acetate gradient in heptane) to give the title compound (290 mg) as a solid. LCMS (Method 1): 398/400 (M + H) ⁺ , retention time 2.17 min. ¹ H-NMR (CDCl ₃ , ppm) 1.38 (3H), 3.70 (3H), 3.99 (2H), 7.18 (1H), 8.71 (1H), 9.20 (1H ).

マイクロ波バイアル中で、１，２−ジメトキシエタン（２ｍｌ）及び水（０．５ｍｌ）中の、２−（５−ブロモ−１−メチル−イミダゾール−２−イル）−３−エチルスルホニル−５−（トリフルオロメチル）ピリジン（１９９ｍｇ、０．５０ｍｍｏｌ）と、（３−（トリフルオロメチル）フェニル）ボロン酸（１４２ｍｇ、０．７５０ｍｍｏｌ）と、炭酸ナトリウム（１５９ｍｇ、１．５００ｍｍｏｌ）との混合物を、５分間にわたってアルゴンでフラッシュした。これに、ＰｄＣｌ₂（ｄｐｐｆ）（１４．６３ｍｇ、０．０２０ｍｍｏｌ）を加え、バイアルを閉じ、１時間にわたって１２０℃で、マイクロ波中で加熱した。反応混合物を酢酸エチルで希釈し、水、塩水で洗浄し、硫酸ナトリウム上で乾燥させ、濃縮した。残渣を、フラッシュカラムクロマトグラフィー（ヘプタン中５〜４０％の酢酸エチル勾配）によってシリカにおいて精製した。生成物を含有する画分を組み合わせて、濃縮し、フラッシュカラムクロマトグラフィー（ジクロロメタン中０〜２．５％のメタノール勾配）によってシリカにおいて再度精製した。生成物を含有する画分を組み合わせて、濃縮し、生成物を、ヘプタンから再結晶化したところ、表題化合物（７２ｍｇ）が固体として得られた（融点１４９〜１５０℃）。ＬＣＭＳ（方法２）：４６４（Ｍ＋Ｈ）⁺，保持時間４．０６ｍｉｎ．¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ｐｐｍ）１．４１（３Ｈ），３．６９（３Ｈ），４．０７（２Ｈ），７．２９（１Ｈ），７．６１−７．７１（３Ｈ），７．７６（１Ｈ），８．７４（１Ｈ），９．１５（１Ｈ）．
表P1: 式(I)の化合物の例 Step 6: Preparation of 3-ethylsulfonyl-2- [1-methyl-5- [3- (trifluoromethyl) phenyl] imidazol-2-yl] -5- (trifluoromethyl) pyridine (title compound P1)

2- (5-Bromo-1-methyl-imidazol-2-yl) -3-ethylsulfonyl-5-, in 1,2-dimethoxyethane (2 ml) and water (0.5 ml) in a microwave vial. A mixture of (trifluoromethyl) pyridine (199 mg, 0.50 mmol), (3- (trifluoromethyl) phenyl) boronic acid (142 mg, 0.750 mmol) and sodium carbonate (159 mg, 1.500 mmol) Flushed with argon for 5 minutes. To this was added PdCl ₂ (dppf) (14.63 mg, 0.020 mmol) and the vial was closed and heated in the microwave at 120 ° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified on silica by flash column chromatography (5-40% ethyl acetate gradient in heptane). Fractions containing product were combined, concentrated and purified again on silica by flash column chromatography (0-2.5% methanol gradient in dichloromethane). Fractions containing the product were combined and concentrated, and the product was recrystallized from heptane to give the title compound (72 mg) as a solid (mp 149-150 ° C.). LCMS (Method 2): 464 (M + H) ⁺ , retention time 4.06 min. ¹ H-NMR (CDCl ₃ , ppm) 1.41 (3H), 3.69 (3H), 4.07 (2H), 7.29 (1H), 7.61-7.71 (3H), 7 .76 (1H), 8.74 (1H), 9.15 (1H).
Table P1: Examples of compounds of formula (I)

表P1(続き): 式(I)の化合物の例

表P2: 式(IIIa)及び(IVa)の中間体の例

Table P1 (continued): Examples of compounds of formula (I)

Table P2: Examples of intermediates of formula (IIIa) and (IVa)

Formulation Example (% = weight percent)
Example F1: Emulsion concentrate

  Any desired concentration of emulsion can be prepared from such a concentrate by dilution with water.

Example F2: Solution

  This solution is suitable for use in the form of fine droplets.

Example F3: Granules

  The active ingredient is dissolved in dichloromethane and the solution is sprayed onto the carrier, after which the solvent is evaporated under reduced pressure.

Example F4: Dust agent

  A ready-to-use dusting agent is obtained by intimately mixing the carrier and the active ingredient.

Example F5: wettable powder

  The active ingredient is mixed with the additives and the mixture is thoroughly ground in a suitable mill. This gives a wettable powder that is diluted with water to give a suspension of any desired concentration.

Example F6: Extruded granule active ingredient: 10%
Sodium lignosulfonate: 2%
Carboxymethyl cellulose: 1%
Kaolin: 87%

  The active ingredient is mixed with additives and the mixture is ground, wetted with water, extruded, granulated and dried in a stream of air.

Example F7: coated granule active ingredient: 3%
Polyethylene glycol (molecular weight 200): 3%
Kaolin: 94%

  In the mixer, the finely divided active ingredient is uniformly applied to the kaolin wetted with polyethylene glycol. This gives a coated granule free of dust.

Example F8: Suspension concentrate active ingredient: 40%
Ethylene glycol: 10%
Nonylphenoxypolyethylene glycol ether (15 mol EO): 6%
Sodium lignosulfonate: 10%
Carboxymethyl cellulose: 1%
37% aqueous formaldehyde solution: 0.2%
Silicone oil (75% aqueous emulsion): 0.8%
Water: 32%

The finely divided active ingredient is intimately mixed with the additive. Suspensions of any desired concentration can be prepared from the suspension concentrate thus obtained by dilution with water.
Example F9: Powder for treatment of dried seeds

  This combination is thoroughly mixed with the adjuvants, and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly for seed treatment.

Example F10: Emulsifiable concentrate active ingredient: 10%
Octylphenol polyethylene glycol ether: 3%
(4-5 moles of ethylene oxide):
Calcium dodecylbenzenesulfonate: 3%
Castor oil polyglycol ether (35 mol ethylene oxide): 4%
Cyclohexanone: 30%
Xylene mixture: 50%

  An emulsion of any required dilution that can be used for plant protection is obtained from this concentrate by dilution with water.

Example F11: flowable active ingredient for seed treatment: 40%
Propylene glycol: 5%
Copolymer butanol PO / EO: 2%
Tristyrene phenol containing 10-20 mol EO: 2%
1,2-benzisothiazolin-3-one (in the form of a 20% solution in water): 0.5%
Monoazo-pigment calcium salt: 5%
Silicone oil (in the form of a 75% emulsion in water): 0.2%
Water: 45.3%

  This micronized combination is intimately mixed with the adjuvant to obtain a suspension concentrate, from which suspension of any desired dilution ratio is obtained by dilution with water. With such dilution, live plants as well as plant propagation material can be treated and protected from microbial infestation by spraying, pouring or dipping.

  The activity of the composition according to the invention can be considerably expanded and adapted to the general situation by adding other insecticidal, acaricidal and / or fungicidal active ingredients. . A further surprising advantage is that mixtures of compounds of the formula I with other insecticidal, acaricidal and / or fungicidal active ingredients may be described in a broader sense as synergistic activity May also have. For example, better tolerance by plants, reduced phytotoxicity, that insects can be controlled at their different stages of development, or during their production, for example during grinding or mixing, during their storage or during their use There is better behavior.

  Suitable additives to the active ingredients herein are typically exemplified by the following types of active ingredients: organophosphorus compounds, nitrophenol derivatives, thiourea, juvenile hormone, formamidine, benzophenone derivatives, urea , Pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

Preferred are the following mixtures of a compound of formula I and the active ingredient (the abbreviation “TX” means “one compound selected from the group consisting of the compounds described in Tables 1 to 6 of the invention”): ):
An auxiliary agent selected from the group of substances consisting of petroleum (alternative name) (628) + TX,
1,1-bis (4-chlorophenyl) -2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenylbenzenesulfonate (IUPAC / chemical abstract name) (1059) + TX, 2-fluoro-N -Methyl-N-1-naphthylacedoamide (IUPAC name) (1295) + TX, 4-chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinosyl (3) + TX, acetoprole [CCN ] + TX, Acrinatrin (9) + TX, Aldicarb (16) + TX, Aldoxycarb (863) + TX, α-Cypermethrin (202) + TX, Amidithione (870) + TX, Amidoflumet [CCN] + TX, Amidothioate (872) + TX, Amit (875) + TX, Amiton hydrogen oxalate (875) + TX, Amitraz (24) + TX, Aramite (881) + TX, Arsenic trioxide (882) + TX, AVI 382 (Compound code) + TX, AZ 60541 (Compound code) + TX Azinphos-ethyl (44) + TX, Azinphos-methyl (45) + TX, Azobenzene (IUPAC name) (888) + TX, Azocyclotin (46) + TX, Azotoate (889) + TX, Benomyl (62) + TX, Benoxafos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, Lomocyclene (918) + TX, Bromophos (920) + TX, Bromophos-ethyl (921) + TX, Bromopropylate (94) + TX, Buprofezin (99) + TX, Butocarboxyme (103) + TX, Butoxycarboxyme (104) + TX, Butyl pyridaben (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphorchlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlor Phenapil (130) + TX, chlorphenetol (968) + TX, chlorfenson (970) + TX, chlorfen sulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzilate (975) + TX, chloromebuform (977) ) + TX, Chloromethyuron (978) + TX, Chloropropyrate (983) + TX, Chlorpyrifos (145) + TX, Chlorpyrifos-methyl (146) + TX, Chlorthiofos (994) + TX, Cineline I (696) + TX, Cineline II (696) + TX Cineline (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (101 ) + TX, kufuranebu (1013) + TX, cyanatoate (1020) + TX, cyflumethofen (CAS registration number: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM ( 1032) + TX, DDT (219) + TX, demefione (1037) + TX, demefione-O (1037) + TX, demefione-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O ( 1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafenthiuron (226) + TX, diariphos (1042) + TX, diazinon (227) + TX, diclofluuride (230) + TX, dichlorvos (236) + TX, diclifos (alternate name) + TX, dichophor (242) + TX, dicrotophos (243) + TX, dienochlor (1071) ) + TX, dimehox (1081) + TX, dimethoate (262) + TX, ginactin (alternate name) (653) + TX, gynex (1089) + TX, gynex-dicrexin (1089) + TX, dinobutone (269) + TX, dinocup (270) + TX , Dinocup-4 [CCN] + TX, Dinocup-6 [CCN] + TX, Dinoctone (1090) + TX, Dinopentone (1092) + TX, Dinosulfone (1097) + TX, Dinoterbon (1098) + TX, Geo Xathione (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfotone (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothione (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethate-methyl (1134) + TX, ethoxazole (320) ) + TX, etrimphos (1142) + TX, phenazafurol (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropatri (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX, fentriphanyl (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrylpyrim (360) + TX Fluazuron (1166) + TX, flubenzimine (1167) + TX, flucycloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, Fluorovenside (1174) + TX, fulvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formatenate hydrochloride (405) TX, formothione (1192) + TX, formparanate (1193) + TX, γ-HCH (430) + TX, gliodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecylcyclopropanecarboxylate (IUPAC / Chemical Abstracts Name) (1216) + TX, Hexithiazox (441) + TX, Iodomethane (IUPAC Name) (542) + TX, Isocarbofos (Alternative Name) (473) + TX, Isopropyl O- (methoxyaminothiophosphoryl) salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, iodofenphos (1248) + TX, phosphorus Dan (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephospholane (1261) + TX, mesulfen (alternate name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathione (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metorcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipahox (1293) + TX, monocrotofos (561) + TX, morphothion (1300) + TX, moxide Chin (alternative name) [CCN] + TX, Nared (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, niflurigide (1309) + TX, niomycin (alternative name) [CCN] + TX, Nitrilacarb (1313) + TX, Nitriracarb 1: 1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxydepro Phos (1324) + TX, Oxydisulfoton (1325) + TX, pp′-DDT (219) + TX, Parathion (615) + TX, Permethrin (626) + TX, Petroleum (alternate name) (628) + TX, Fencapton (1330) + TX , Fent A (631) + TX, Folate (636) + TX, Hosalon (637) + TX, Phosphorane (1338) + TX, Phosmet (638) + TX, Phosphamidone (639) + TX, Hoxime (642) + TX, Pirimiphos-methyl (652) + TX, Poly Chloroterpene (common name) (1347) + TX, Polynactin (alternative name) (653) + TX, Prochronol (1350) + TX, Profenofos (662) + TX, Promasil (1354) + TX, Propargit (671) + TX, Propetanephos (673) ) + TX, propoxer (678) + TX, protidathione (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrin (696) + TX, pyridabe (699) + TX, pyridafenthione (701) + TX, pyrimidifen (706) + TX, pyrimidate (1370) + TX, quinalphos (711) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, shuradan (1389) + TX, Cebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, Sofamid (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternate name) [CCN] + TX, sulfuramide (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, τ-fulvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, telbum (alternative Name) + TX, tetrachlorvinphos (777) + TX, tetradiphone (786) + TX, tetranactin (alternative name) (653) + TX, tetrasulfur (1425) + TX, thiaphenox (alternative name) + TX, thiocarboxyme (1431) + TX, thiophanox (800) + TX, thiomethone (801) + TX, thioquinox (1436) + TX, thuringiensine (alternative name) [CCN] + TX, triamiphos (1441) + TX, trialatin (1443) + TX, triazophos (820) TX, Triazuron (alternate name) + TX, Trichlorfone (824) + TX, Trifenofos (1455) + TX, Trinactin (alternate name) (653) + TX, Bamidthione (847) + TX, Vaniliprol [CCN] and YI-5302 (Compound code) + TX An acaricide selected from the group of substances consisting of:
Betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dicron (1052) + TX, dichlorophen (232) + TX, endtal (295) + TX , Fentin (347) + TX, slaked lime [CCN] + TX, narvum (566) + TX, quinoclamin (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and water An algicidal agent selected from the group of substances consisting of triphenyltin oxide (IUPAC name) (347) + TX,
Abamectin (1) + TX, Kurumato (1011) + TX, Doramectin (alternative name) [CCN] + TX, Emamectin (291) + TX, Emamectin benzoate (291) + TX, Eprinomectin (alternate name) [CCN] + TX, Ivermectin (alternative) Name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) an anthelmintic selected from the group of substances consisting of + TX,
A biocide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridine-4-amine (IUPAC name) (23) and strychnine (745) + TX,
1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX , Dodisine (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrolgaphene (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis ( Dimethyldi Ocarbamate) (IUPAC name) (1308) + TX, nitrapirine (580) + TX, octylinone (590) + TX, oxophosphoric acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole ( 658) + TX, streptomycin (744) + TX, sesquisulfate streptomycin (744) + TX, teclophthalam (766) + TX, and thiomersal (alternative name) [CCN] + TX, a fungicide selected from the group
Adoxophys orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (Alternative name) (19) + T Anagrapha falcifera, NPV (alternative name) (28) + TX, Anagras atomus (alternative name) (29) + TX, Aphelinus abdominalis (Apelinus) 33 (alternative name) , Aphidius Colemani (alternative name) (34) + TX, Aphidletes aphidimiza (Aphi) doletes aphidimiza) (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus films (alternative name) (48) + TX, bacillus Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subspecies Isp ais wai (Scientific name) (51) + TX, Bacillus thuringiensis subsp. (Bacillus thuringiensis subsp. Isralensis) (scientific name) (51) + TX, Bacillus thuringiensis subspecies Japonensis (scientific name) (51) + TX, Bacillus thurgen spp. ) (Scientific name) (51) + TX, Bacillus thuringiensis subsp. Tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX (Beauuveria brownniarti) (alternative name) (54) + TX, Chrysopera carnea (alternate name) (151) + TX, tsumatoa monkey ladybug (Cryptolaemus montroin diT17) pomonella) GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isea (alternative name) (254) + TX, ) (Scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, America tobacco budworm (Helicoverpa zea) NPV (alternative name) (431) + TX, hetero Love di Sevilla-bacteriophage follower La (Heterorhabditis bacteriophora) and H. H. megidis (alternate name) (433) + TX, Hippodamia congenens (alternate name) (442) + TX, Leptomastics dactilopii (alternate name) (48 + T)・ Carrophynus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) X Acrylum (Metalhizium anisopliae var. Acidum) (scientific name) (523) + TX, Metarhizium anisoprie var. Anisoprie (scientific name) (523) + TX, Neodipion sertifer NPV and N. N. lecontei NPV (alternative name) (575) + TX, Orius spp. (Alternate name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Chili Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multi-capsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinerema bibionis (Stenernema bineis) Steinernema carpocapsae (alternative name) (742) + TX, Steinerne Ferch Steinerne feltiae (alternate name) (742) + TX, Steinernema glasseri (alternate name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX Steinerema riobravis (alternate name) (742) + TX, Steinerne scapterisci (alternate name) (742) + TX, Steinernema spp. (Alternate name) X (Traco) ) (Alternative name) (826) + TX, Tiflodroms Occidentalis (Typ Lodromus occidentalis) (alternative name) (844) and Verticillium potassium-Rekani (Verticillium lecanii) (alternative name) (848) + biological agent selected from the group of materials consisting of TX,
A soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX;
Aphorate [CCN] + TX, Bisadil (alternate name) [CCN] + TX, Busulfan (alternate name) [CCN] + TX, Diflubenzuron (250) + TX, Dimatif (alternate name) [CCN] + TX, Hemel [CCN] + TX, Hempa [CCN] + TX, Metepa [CCN] + TX, Methiotepa [CCN] + TX, Methyl Afolate [CCN] + TX, Morgide [CCN] + TX, Penfluron (alternative name) [CCN] + TX, Tepa [CCN] + TX, Thiohempa (alternative Name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX, a fertility agent selected from the group of substances,
(E) -dec-5-en-1-yl acetate and (E) -dec-5-en-1-ol (IUPAC name) (222) + TX, (E) -tridec-4-en-1-yl Acetate (IUPAC name) (829) + TX, (E) -6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E, Z) -tetradeca-4,10-diene-1- Ile acetate (IUPAC name) (779) + TX, (Z) -Dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z) -Hexadeca-11-enal (IUPAC name) (436) + TX, (Z) -hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z) -hexadec-13-en-11-in-1-yl acetate (IU (AC name) (438) + TX, (Z) -icosa-13-en-10-one (IUPAC name) (448) + TX, (Z) -tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z) -tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z) -tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E, 9Z) -Dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z, 11E) -Tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX (9Z, 12E) -Tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadeca-1-ene (IUPAC) ) (545) + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one (IUPAC name) (544) + TX, α-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [ CCN] + TX, Codroreua (alternate name) [CCN] + TX, Codremon (alternate name) (167) + TX, Culua (alternate name) (179) + TX, Disparrua (277) + TX, Dodec-8-en-1-yl Acetate (IUPAC name) (286) + TX, dodeca-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, Dominical lure (alternate name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + X, eugenol (alternate name) [CCN] + TX, frontalin (alternate name) [CCN] + TX, gossip lure (alternate name) (420) + TX, grand lure (421) + TX, grand lure I (alternate name) (421) + TX , Grand Lure II (alternate name) (421) + TX, Grand Lure III (alternate name) (421) + TX, Grand Lure IV (alternate name) (421) + TX, Hexalure [CCN] + TX, Ipsdienol (alternative name) [CCN] + TX, ipsenol (alternate name) [CCN] + TX, japonilua (alternate name) (481) + TX, lineatin (alternate name) [CCN] + TX, little aur (alternate name) [CCN] + TX, lulua (alternative name) [CCN] + TX, medrua [CCN] + TX, megatomoic acid (alternate name) [CCN] + TX, methyl Igenol (alternative name) (540) + TX, Muscarua (563) + TX, octadec-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadec-3,13-dien-1-yl acetate ( IUPAC name) (589) + TX, Orfuralua (alternative name) [CCN] + TX, Orchitala (alternative name) (317) + TX, Ostramon (alternative name) [CCN] + TX, Sigurua [CCN] + TX, Solzidine (alternative name) ( 736) + TX, sulfatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedorua (839) + TX, trimedorua A (alternative name) (839) + TX, Trimedorua B ₁ (Alternative name) (839) + TX, Trimedorua B ₂ (Alternate name) (839) + TX, trimedorua C (alternate name) (839) and trunk-call (alternate name) insect pheromone selected from the group of substances consisting of [CCN] + TX,
2- (octylthio) ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX Dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbate [CCN] + TX, dimethyl [CCN] + TX, ethylhexanediol (1137) + TX, hexaamide [CCN] + TX An insect repellent selected from the group of substances consisting of: methkin-butyl (1276) + TX, methyl neodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,
1-dichloro-1-nitroethane (IUPAC / chemical abstract name) (1058) + TX, 1,1-dichloro-2,2-bis (4-ethylphenyl) ethane (IUPAC name) (1056), + TX, 1 , 2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC) / Chemical Abstracts Name) (916) + TX, 2,2,2-trichloro-1- (3,4-dichlorophenyl) ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinyl Ethylmethyllphosphate (IUPAC name) (1066) + TX, 2- (1 3-dithiolan-2-yl) phenyldimethylcarbamate (IUPAC / chemical abstract name) (1109) + TX, 2- (2-butoxyethoxy) ethyl thiocyanate (IUPAC / chemical abstract name) (935) + TX, 2 -(4,5-dimethyl-1,3-dioxolan-2-yl) phenylmethylcarbamate (IUPAC / chemical abstract name) (1084) + TX, 2- (4-chloro-3,5-xylyloxy) ethanol ( IUPAC name) (986) + TX, 2-chlorovinyldiethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindane-1,3-dione (IUPAC name) ) (1246) + TX, 2-methyl (pro 2-Inyl) aminophenylmethylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-Methyl-1-phenylpyrazol-5-yldimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl (prop-2-ynyl) amino-3,5-xylylmethylcarbamate (IUPAC) Name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX , Acetion (alternate name) [CCN] + TX, Acetop Roll [CCN] + TX, Acrinatrin (9) + TX, Acrylonitrile (IUPAC name) (861) + TX, Alanicarb (15) + TX, Aldicarb (16) + TX, Aldoxycarb (863) + TX, Aldrin (864) + TX, Areslin ( 17) + TX, allosamidine (alternative name) [CCN] + TX, arixicarb (866) + TX, α-cypermethrin (202) + TX, α-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidithione (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidathione (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinephos-ethyl (44) + TX, azinephos-methyl (45) + TX, Azotoate (889) + TX, Bacillus thuringiensis delta endotoxin (alternative name) (52) + TX, barium hexafluorosilicate (alternate name) [CCN] + TX, barium polysulfide (IUPAC / chemical abstracts) Name) (892) + TX, Bartholin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, Bengiocarb (58) + TX, Ben Racarb (60) + TX, bensultap (66) + TX, β-cyfluthrin (194) + TX, β-cypermethrin (203) + TX, bifenthrin (76) + TX, bioarethrin (78) + TX, bioarethrin S-cyclopentenyl isomer (alternative) Name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis (2-chloroethyl) ether (IUPAC name) (909) + TX, bistriflulone (83 ) + TX, borax (86) + TX, brofenvalerate (alternate name) + TX, bromfenvinphos (914) + TX, bromocyclene (918) + TX, bromo-DDT (alternate name) [CCN] + TX, bromophos (920) + TX, bromophos-eth (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, porcine carb (926) + TX, butathiophos (927) + TX, butcarboxyme (103) + TX, butonate (932) + TX, butoxycarboxyme (104) + TX , Butylpyridaben (alternative name) + TX, Kazusafos (109) + TX, Calcium arsenate [CCN] + TX, Calcium cyanide (444) + TX, Calcium polysulfide (IUPAC name) (111) + TX, Camphorchlor (941) + TX, Carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / chemical abstract name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenoch On (947) + TX, Carbosulfurne (119) + TX, Cartap (123) + TX, Cartap Hydrochloride (123) + TX, Sebazine (alternate name) (725) + TX, Chlorbicyclen (960) + TX, Chlordan (128) + TX, Chlordecone (963) + TX, Chlordimeform (964) + TX, Chlordimeform Hydrochloride (964) + TX, Chlorethoxyphos (129) + TX, Chlorfenapyr (130) + TX, Chlorfenvin Phos (131) + TX, Chlorfluazuron ( 132) + TX, chlormefos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxime (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifo -Methyl (146) + TX, Chlorthiophos (994) + TX, Chromafenozide (150) + TX, Cineline I (696) + TX, Cineline II (696) + TX, Cineline (696) + TX, Cis-resmethrin (alternative name) + TX, cismethrin ( 80) + TX, Crocitrin (alternate name) + TX, Chloetocarb (999) + TX, Crosantel (alternate name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, cumitoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, Kurfomate (1011) + TX, cryolite (alternative name) ) (177) + TX, CS 7 8 (development code) (1012) + TX, cyanophenphos (1019) + TX, cyanophos (184) + TX, cyanatoate (1020) + TX, citrine [CCN] + TX, cycloprotorin (188) + TX, cyfluthrin (193) + TX, Cyhalothrin (196) + TX, Cypermethrin (201) + TX, Ciphenothrin (206) + TX, Cyromazine (209) + TX, Cythioate (alternate name) [CCN] + TX, d-limonene (alternate name) [CCN] + TX, d− Tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, Dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefione (1037) + TX, demefi -O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton- S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, difenthiuron (226) + TX, diariphos (1042) + TX, diamidaphos (1044) + TX, diazinon ( 227) + TX, dicapton (1050) + TX, diclofenthion (1051) + TX, dichlorvos (236) + TX, dicrifos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanyl (244) + TX Jie Ludrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilol (alternate name) [CCN] + TX, dimeflutrin [CCN] + TX, dimefox (1081) ) + TX, dimethane (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimethylane (1086) + TX, dinex (1089) + TX, dinex-dicrexin (1089) + TX, dinoprop (1093) + TX, dinosum (1094) + TX, dinocebu (1095) + TX, dinotefuran (271) + TX, diophenolane (1099) + TX, dioxabenzophos (1100) + TX, dioxa Rub (1101) + TX, Dioxathion (1102) + TX, Disulfoton (278) + TX, Diticlofos (1108) + TX, DNOC (282) + TX, Doramectin (alternate name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) ) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, Endothion (1121) + TX, Endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, Epofenonan (1124) + TX, Eprinomectin (alternate name) [CCN] + TX, Esphef Valerate (302) + TX, ethafos (alternate name) [CCN] + TX, etiophencarb (308) + TX, ethione (309) + TX, ethiprole (310) + TX, ethoate-methyl (1134) + TX, etoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofene Prox (319) + TX, Etrimfos (1142) + TX, EXD (1143) + TX, Fan Fur (323) + TX, Phenamifos (326) + TX, Phenazaflor (1147) + TX, Fenchlorfos (1148) + TX, Phenetacarb ( 149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, phenoxacrim (1153) + TX, phenoxycarb (340) + TX, fenpyritrin (1155) + TX, fenpropatoline (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX Flubendiamide (CAS. Registration number: 272451-65-7) + TX, flucofuron (1168) + TX, flucycloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenerim [CCN] + TX, flufenoxuron ( 370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fulvalinate (1184) + TX, FMC 1137 (development code)
(1185) + TX, Phonophos (1191) + TX, Formethanate (405) + TX, Formateate hydrochloride (405) + TX, Formothion (1192) + TX, Formparanate (1193) + TX, Phosmethylan (1194) + TX, Hospirate (1195) + TX, Phostiazate (408) + TX, Phosthiethane (1196) + TX, Furatiocarb (412) + TX, Frethrin (1200) + TX, γ-Cyhalothrin (197) + TX, γ-HCH (430) + TX, Guazatine (422) + TX, Guazatine acetate (422) ) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptac Lor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) ) + TX, hikincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231) + TX , Isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodoline (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + X, isopropyl O- (methoxyaminothiophosphoryl) salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, Jasmolin II (696) + TX, iodofenphos (1248) + TX, juvenile hormone I (alternate name) [CCN] + TX, juvenile hormone II (alternate name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, Keleban (1249) + TX, quinoprene (484) + TX, λ-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, Lindan (430) + TX, Lilimfos (1251) + TX, Rufenuron (490) + TX, Ritidathione (1253) + TX, m-cumenylmethylcarbamate (IUPAC name) (1014) + TX, Magnesium phosphide (IUPAC name) (640) + TX, Malathion (492) ) + TX, malonoben (1254) + TX, majidox (1255) + TX, mecarbam (502) + TX, mecarphone (1258) + TX, menazone (1260) + TX, mephospholane (1261) + TX, mercuric chloride (513) + TX, mesulfenphos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternate name) (519) + TX, metam-sodium (519) + TX, methaclifos (1266) + TX, meta Dofos (527) + TX, methanesulfonyl fluoride (IUPAC / chemical abstract name) (1268) + TX, methidathione (529) + TX, methiocarb (530) + TX, methocrothos (1273) + TX, methomyl (531) + TX, methoprene ( 532) + TX, methokine-butyl (1276) + TX, methotrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyphenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, Methyl chloroform (alternate name) [CCN] + TX, methylene chloride [CCN] + TX, metfurthrin [CCN] + TX, metorcarb (550) + TX, methoxadiazone (1288) + TX, mevinphos (556) + T , Mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipahox (1293) + TX, milex (1294) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (Alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nared (567) + TX, naphthalene (IUPAC / chemical abstract name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, niflulidide (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitriracarb (1313) + TX, Nitrilacarb 1: 1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (common name) (1319) + TX, Novallon (585) + TX Nobiflumuron (586) + TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057) + TX, O, O-diethyl O-4-methyl-2-oxo-2H- Chromen-7-yl phosphorothioate (IUPAC name) (1074) + TX, O, O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, O, O, O ′ , O′-Tetrapropyldithiopyrophosphate (IUPAC ) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprophos (1324) + TX, oxydisulfotone (1325) + TX, pp′-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penflurone (alternate name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum (alternate name) (628) + TX, PH 60-38 (development code) (1328) + TX, fencapton (1330) + TX , Fe Thrin (630) + TX, Fentate (631) + TX, Folate (636) + TX, Hosalon (637) + TX, Phosphorane (1338) + TX, Phosmet (638) + TX, Phosniclor (1339) + TX, Phosphamidone (639) + TX, Phosphine (IUPAC name) (640) + TX, oxime (642) + TX, oxime-methyl (1340) + TX, pyrimetaphos (1344) + TX, pyrimicarb (651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX , Polychlorodicyclopentadiene isomer (IUPAC name) (1346) + TX, polychloroterpene (common name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX Praretrin (655) + TX, plecocene I (alternate name) [CCN] + TX, plecocene II (alternate name) [CCN] + TX, plecocene III (alternate name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX , Profluthrin [CCN] + TX, promasil (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetanephos (673) + TX, propoxer (678) + TX, protidathione (1360) + TX, prothiophos (686) + TX, protophos (1362) + TX, protrifen bute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazofos (693) + TX, pyrethmethrin (1367) + TX, pi Letrin I (696) + TX, pyrethrin II (696) + TX, pyrethrin (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridafenthione (701) + TX, pyrimidifene (706) + TX, pyrimidate (1370) + TX, Pyriproxyfen (708) + TX, Quassia (alternate name) [CCN] + TX, quinalphos (711) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quinthiophos (1381) + TX, R-1492 (development code) ) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) 1386) + TX, riania (alternative name) (1387) + TX, ryanodine (common name) (1387) + TX, sabadilla (alternative name) (725) + TX, shuradan (1389) + TX, Cebufos (alternative name) + TX, selamectin (alternative) Name) [CCN] + TX, SI-0009 (Compound code) + TX, SI-0205 (Compound code) + TX, SI-0404 (Compound code) + TX, SI-0405 (Compound code) + TX, Silafluophene (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC / chemical abstract name) (1399) + TX, sodium hexafluorosilicate ( 1400) + TX, Nat Umpentachlorophenoxide (623) + TX, Sodium selenate (IUPAC name) (1401) + TX, Sodium thiocyanate [CCN] + TX, Sofamid (1402) + TX, Spinosad (737) + TX, Spiromesifene (739) + TX, Spirotetra Mato (CCN) + TX, Sulcofuron (746) + TX, Sulcofuron-Sodium (746) + TX, Sulfuramide (750) + TX, Sulfotep (753) + TX, Sulfuryl fluoride (756) + TX, Sulproos (1408) + TX, Tar oil (alternative) Name) (758) + TX, τ-fulvalinate (398) + TX, Tadimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, TE Pyrimfos (764) + TX, Teflubenzuron (768) + TX, Tefluthrin (769) + TX, Temefos (770) + TX, TEPP (1417) + TX, Teraretrin (1418) + TX, Terbum (alternative name) + TX, Terbufos (773) + TX, Tetra Chloroethane [CCN] + TX, tetrachlorbinphos (777) + TX, tetramethrin (787) + TX, θ-cypermethrin (204) + TX, thiacloprid (791) + TX, thiaphenox (alternative name) + TX, thiamethoxam (792) + TX , Ticlofos (1428) + TX, thiocarboxyme (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800 ) + TX, thiomethone (801) + TX, thionazine (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensine (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX , Transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazolone (alternate name) + TX, trichlorfone (824) + TX, trichlormetaphos -3 (alternative name) [CCN] + TX, trichloronate (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimetacarb (840) + T , Triprene (1459) + TX, bamidthione (847) + TX, vaniliprol [CCN] + TX, veratridine (alternate name) (725) + TX, veratrine (alternate name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX ,
YI-5302 (compound code) + TX, ζ-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprophos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, sienopyrafen [560121-52-0] + TX, cyflumethofen [400882-07-7] + TX, pyrifluquinazone [337458 -27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxafurol [946578-00-3] + TX Flupiprol [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfurthrin [84937-88-2] + TX, triflumezopyrim (disclosed in International Publication No. 2012/092115) + TX, Fluxamethamide (Pamphlet of International Publication No. 2007/026965) + TX, ε-methfurthrin [240494-71-7] + TX, ε-mon fluorotrin [1065124-65-3] + TX, fluazaindolizine [12554304- 22-7] + TX, chloropraretrin [399572-87-3] + TX, fluxamethamide [928783-29-3] + TX, cyhalodiamide [1262605-53-7] + TX, chi Xazafen [3304559-31-9] + TX, brofuranilide [1207727-04-5] + TX, flufiprol [704886-18-0] + TX, cyclanilipol [1031756-98-5] + TX, tetraniliprolol [12296654] -66-3] + TX, guadipyr (described in WO2010 / 060231 pamphlet) + TX, cycloxapride (described in WO2005 / 077934 pamphlet) + TX Pesticides,
Bis (tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloecarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, Pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tadim carb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetaca Selected from the group consisting of: (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprol [394730-71-3] + TX Molluscicide,
AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / chemical abstract name) (1045) + TX, 1,2-dichloropropane (IUPAC / chemical abstract name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts Name) (1065) + TX, 3- (4-Chlorophenyl) -5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinane-3 -Ilacetic acid (IUPAC name) (1286) + TX, 6-isopenteni Aminopurine (alternative name) (210) + TX, Abamectin (1) + TX, Acetoprole [CCN] + TX, Alanikalb (15) + TX, Aldicarb (16) + TX, Aldoxycarb (863) + TX, AZ 60541 (Compound code) + TX, Bencrothiaz [CCN] + TX, Benomyl (62) + TX, Butylpyridaben (alternative name) + TX, Kazusafos (109) + TX, Carbofuran (118) + TX, Carbon disulfide (945) + TX, Carbosulfan (119) + TX, Chloropicrin (141) + TX, Chlorpyrifos (145) + TX, Chloecarb (999) + TX, Cytokinin (alternative name) (210) + TX, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamida (1044) + TX, Diclofenthion (1051) + TX, Dicrifos (alternative name) + TX, Dimethoate (262) + TX, Doramectin (alternative name) [CCN] + TX, Emamectin (291) + TX, Emamectin benzoate (291) + TX, Eprinomectin (alternate name) [CCN] + TX, etoprophos (312) + TX, ethylene dibromide (316) + TX, phenamiphos (326) + TX, fenpyrad (alternate name) + TX, fensulfothione (1158) + TX, phostiazate (408) + TX, Phoschietane (1196) + TX, Furfural (alternate name) [CCN] + TX, GY-81 (Development code) (423) + TX, Heterophos [CCN] + TX, Iodomethane (IUPAC name) (542) + TX, Isamidephos 1230) + TX, Isazofos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metam-potassium (alternative name) ( 519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, mulberry Mycobacterium verrucaria composition (alternate name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, folate (636) + TX, phosphamidone (639) + TX, phosphocarb [CCN] + T , Cebufos (alternative name) + TX, Seramectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbum (alternative name) + TX, Terbufos (773) + TX, Tetrachlorothiophene (IUPAC / Chemical Abstracts name) ( 1422) + TX, thiaphenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, xylenol [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) ) (210) + TX, nematicide selected from the group of substances consisting of fluenesulfone [318290-98-1] + TX,
A nitrification inhibitor selected from the group of substances consisting of potassium ethyl xanthate [CCN] and nitrapiline (580) + TX;
A plant activator selected from the group of substances consisting of acibenzoral (6) + TX, acibenzoral-S-methyl (6) + TX, probenazole (658) and reynoutia sachalinensis extract (alternative name) (720) + TX,
2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, Aluminum phosphide (640) + TX, antu (880) + TX, diarsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifakoum (89) + TX, bromazirone (91 ) + TX, brometaline (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorofacinone (140) + TX, cholecalciferol (alternate name) (850) + TX, cumulolol (1004) + TX, Bear frill (1005) + T , Coumatetralyl (175) + TX, Crimidine (1009) + TX, Diphenacoum (246) + TX, Diphethialone (249) + TX, Difacinone (273) + TX, Ergocalciferol (301) + TX, Flocumafen (357) + TX, Fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, Lindane (430) + TX, Magnesium phosphide (IUPAC name) (640) + TX, Methyl bromide (537) + TX, Norbornide (1318) + TX, Hosacetim (1336) + TX, Phosphine (IUPAC name) (640) + TX, phosphorous [CCN] + TX, pindon (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sililoside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide A rodenticide selected from the group of substances consisting of (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX;
2- (2-butoxyethoxy) ethyl piperonylate (IUPAC name) (934) + TX, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone (IUPAC name) ) (903) + TX, farnesol and nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piperotal ( 1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesamorin (1394) and sulfoxide (1406) + TX ,
Anthraquinone (32) + TX, Chloralose (127) + TX, Copper naphthenate [CCN] + TX, Copper oxychloride (171) + TX, Diazinon (227) + TX, Dicyclopentadiene (chemical name) (1069) + TX, Guazatine (422) + TX, Guazatine acetate (422) + TX, Methiocarb (530) + TX, Pyridin-4-amine (IUPAC name) (23) + TX, Tyram (804) + TX, Trimetacarb (840) + TX, Zinc naphthenate [CCN] and Diram ( 856) an animal repellent selected from the group of substances consisting of + TX,
A virusicide selected from the group of substances consisting of iminein (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
A wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octyrinone (590) and thiophanate-methyl (802) + TX,
And azaconazole (60207-31-0) + TX, viteltanol [70585-36-3] + TX, bromconazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68] -3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, fluquinconazole [136426-54-5] + TX , Flusilazole [85509-19-9] + TX, flutriazole [76667-21-0] + TX, hexaconazole [79983-71-4] + TX, imazalyl [3554-44-0] + TX, imibenconazole [86598] 92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [125116-23-6] + TX, microbutanyl [88671-89-0] + TX, pefazoate [101903-30-4] + TX, penconazole [66246- 88-6] + TX, prothioconazole [1788928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, cimeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimephone [43121-43-3] + TX, triadimenol [5521 -65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ansimidol [12771-68-5] + TX, fenarimol [60168-88-9. ] + TX, Nuarimol [63284-71-9] + TX, Bupirimate [41483-43-6] + TX, Dimethylylmol [5221-53-4] + TX, Ethymol [23947-60-6] + TX, Dodemorph [1593-77-7 ] + TX, fenpropidin [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552] -61-2] + TX, mepanipiri [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpicuronyl [74738-17-3] + TX, fludioxonyl [133134-86-1] + TX, benalaxyl [71626-11-4] + TX, Fulleraxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, off-race [58810-48-3] + TX, oxadixyl [77732-09-3 ] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79- 8] + TX, black Linate [84332-86-5] + TX, Diclozoline [24201-58-9] + TX, Iprodione [36734-19-7] + TX, Microzoline [54864-61-8] + TX, Procymidone [32809-16-8] + TX , Vinclozoline [50471-44-8] + TX, Boscalid [188425-85-6] + TX, Carboxin [5234-68-4] + TX, Fenfram [24691-80-3] + TX, Flutolanil [66332-96-5] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, tifluzamide [130000-40-7] + TX, guazatine [108173-90- 6] + TX Dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctazine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [1499961 -52-4] + TX, enesterobrin {Proc. BCPC, Int. Congr. , Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, cresoxime-methyl [143390-89-0] + TX, methinostrobin [133408-50-1] + TX, trifloxy Strobin [141517-21-7] + TX, Orizastrobin [248593-16-0] + TX, Picoxystrobin [117428-22-5] + TX, Pyraclostrobin [175013-18-0] + TX, Felvam [ 14484-64-1] + TX, Mancozeb [8018-01-7] + TX, Maneb [12427-38-2] + TX, Methylam [9006-42-2] + TX, Propineb [12071-83-9] + TX, Tiram [ 137-26-8] + TX, Zineb [1212 -67-7] + TX, diram [137-30-4] + TX, captahol [2425-06-1] + TX, captan [133-06-2] + TX, diclofluanide [1085-98-9] + TX, fluoro Imido [41205-21-4] + TX, Holpet [133-07-3] + TX, Tolylfuranide [731-27-1] + TX, Bordeaux solution [8011-63-0] + TX, Copper hydroxide [20427-59- 2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine copper [10380-28-6] + TX, dinocup [131-72-6] + TX, nitrotar-iso Lopyr [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolcrofos-methyl [57018-04-9] + TX, acibenzoral-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, Benchia Valicarb [413615-35-7] + TX, Blasticidin-S [2079-00-7] + TX, Quinomethionato [2439-01-2] + TX, Chloroneb [2675-77-6] + TX, Chlorothalonyl [1897-45 −6] + TX, cyflufenamide [1 80409-60-3] + TX, simoxanyl [57966-95-7] + TX, dicron [117-80-6] + TX, diclocimet [13920-32-4] + TX, dichromedin [62885-36-5] + TX, dichlorane [ 99-30-9] + TX, dietofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (furmorph) [21867-47-9] + TX, dithianone [3347-22-6 ] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, phenoxanyl [115852-48-7 ] + X, fentin [668-34-8] + TX, ferrimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, fursulfamide [106917-52-6] + TX, fenhexamide [126833-3-17-8] + TX, fosetyl-aluminum [39148-24-8] + TX, hymexazole [10004-44-1] + TX, iprovaricarb [140923-17-7] + TX, IKF-916 ( Cyazofamid) [120116-88-3] + TX, kasugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metolaphenone [220899-03-6] + TX, pencylone [66063-05 6] + TX, phthalide [27355-22-2] + TX, polyoxin [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12- 4] + TX, Pyroxylone [57369-32-1] + TX, Quinoxyphene [124495-18-7] + TX, Kintozen [82-68-8] + TX, Sulfur [7704-34-9] + TX, Thiazinyl [223580-51- 6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triphorin [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052 -6 8-5] + TX, Mandipropamide [374726-62-2] + TX, Isopyrazam [8816885-58-1] + TX, Sedaxane [874967-67-6] + TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4 -Carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl) -amide (disclosed in WO 2007/048556) + TX, 3 -Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3 ', 4', 5'-trifluoro-biphenyl-2-yl) -amide (disclosed in WO 2006/087343) ) + TX, [(3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS) -3- [ Ropropylcarbonyl) oxy] -1,3,4,4a, 5,6,6a, 12,12a, 12b-decahydro-6,12-dihydroxy-4,6a, 12b-trimethyl-11-oxo-9- ( 3-pyridinyl) -2H, 11H naphtho [2,1-b] pyrano [3,4-e] pyran-4-yl] methyl-cyclopropanecarboxylate [915972-17-7] + TX and 1,3,5 -Trimethyl-N- (2-methyl-1-oxopropyl) -N- [3- (2-methylpropyl) -4- [2,2,2-trifluoro-1-methoxy-1- (trifluoromethyl) ) Ethyl] phenyl] -1H-pyrazole-4-carboxamide [926914-55-8] + TX biologically active compound selected from the group of substances.

  A reference number in square brackets after the active ingredient, for example, [3878-19-1], means a chemical abstract registration number. The above mixing partners are known. The active ingredient is “The Pesticide Manual” [The Pesticide Manual-A World Compendium; D. S. Tomlin; the British Crop Protection Council, they are listed therein with the item numbers shown in parentheses above for certain compounds; for example; The compound “abamectin” is described under item number (1). When “[CCN]” is added to a specific compound in the above, the corresponding compound is included in “Compendium of Pesticide Common Names”, which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, (Copyright) 1995-2004]; for example, the compound “acetoprole” has an Internet address: http: // www. alanwood. net / pesticides / acetoprole. It is described in html.

  Most of the above active ingredients are referred to above by the so-called “generic name”, the related “ISO common name” or another “common name” being used in individual cases. Where the notation is not “generic name”, the notation property used instead is shown in parentheses for the particular compound; in that case, IUPAC name, IUPAC / chemical abstract name, “chemical name”, “ Where "common names", "compound names" or "development codes" are used, or when one of those notations is not used and "generic names" are not used, "alternate names" are used. “CAS registration number” means a chemical abstract registration number.

  The active ingredient mixture of the compound of formula I selected from Tables 1 to 6 and the above active ingredient is preferably a compound selected from Tables 1 to 6 and the above active ingredient, preferably 100: 1 to 1: 6000, in particular 50: 1 to 1:50, more particularly 20: 1 to 1:20, even more particularly 10: 1 to 1:10, very particularly 5: 1 and 1: 5. (A ratio of 2: 1 to 1: 2 is particularly preferred, a ratio of 4: 1 to 2: 1 is likewise preferred), in particular 1: 1 or 5: 1 or 5: 2 or 5 : 3, or 5: 4, or 4: 1, or 4: 2, or 4: 3, or 3: 1, or 3: 2, or 2: 1, or 1: 5, or 2: 5, or 3. : 5, or 4: 5, or 1: 4, or 2: 4, or 3: 4, or 1: 3, or 2: 3, or 1: 2, or 1: 600, or 1: 300. Or 1: 150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1: 6000, or 1: 3000, or 1: 1500, Or in a ratio of 1: 350, or 2: 350, or 4: 350, or 1: 750, or 2: 750, or 4: 750. Their mixing ratio is based on mass.

  The above mixture may be used in a method for controlling pests, the method comprising applying a composition comprising the above mixture to the pest or its environment, but by surgery or treatment Excludes methods for the treatment of the animal body and diagnostic methods performed in the human or animal body.

  A mixture comprising a compound of formula I selected from Tables 1-6 and one or more active ingredients as described above is, for example, in a single ready-mix form, such as a “tank mix” Of a single active ingredient as a combined spray mixture composed of separate formulations of a single active ingredient and when applied sequentially, ie one after another in a fairly short period of time such as hours or days Can be applied in combination. The order in which the compounds of Formula I selected from Tables 1-6 and the active ingredients described above are applied is not critical to the practice of the invention.

  The composition according to the invention comprises a stabilizer, for example a non-epoxidized or epoxidized vegetable oil (for example epoxidized coconut oil, rapeseed oil or soybean oil), an antifoaming agent, for example silicone oil, a preservative, a viscosity modifier, Binders and / or tackifiers, fertilizers or other active ingredients for obtaining a specific effect, such as fungicides, fungicides, nematicides, plant activators, molluscicides or herbicides Additional solid or liquid auxiliaries can also be included.

  The composition according to the invention can be prepared in the absence of an auxiliary agent, for example by grinding, sieving and / or compressing the solid active ingredient and, for example, the active ingredient in one or more auxiliary agents. In a manner known per se in the presence of at least one auxiliary agent. These methods for the preparation of this composition and the use of Compound I for the preparation of these compositions are also the subject of the present invention.

  Application methods for this composition, ie spraying, atomizing, spraying, brushing on, dressing, scattering or pouring (these are generally The use of the composition for controlling pests of the type described above, and the use of the composition for controlling pests of the type described above. It is another subject of the invention. Typical concentration ratios are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm of active ingredient. The application rate per hectare is generally 1-2000 g of active ingredient per hectare, in particular 10-1000 g / ha, preferably 10-600 g / ha.

  A preferred method of application in the field of crop protection is application to the foliage of plants (foliar application), and the application frequency and application rate can be selected according to the risk of infestation by the corresponding pests. Alternatively, the active ingredient is introduced by irrigating the liquid composition into the plant habitat or the solid form of the active ingredient is introduced into the plant habitat, eg soil, eg in the form of granules (soil application). ) Can reach the plant via the root system (systemic action). In the case of paddy rice plants, such granules can be metered into paddy fields.

  The compounds according to the invention and the compositions thereof are also suitable for the protection of plant propagation material, for example seeds such as fruits, tubers or grains, or seedlings from the above-mentioned types of pests. The propagation material can be treated with this compound prior to planting, for example, the seed can be treated before sowing. Alternatively, the compound can be applied to the seeds by immersing the seeds in a liquid composition or by applying a layer of a solid composition (coating). If the propagation material is to be planted at the site of application, the composition can also be applied to the furrow, for example during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are a further subject of the present invention. Typical treatment rates depend on the plant and the pest / fungus to be controlled and are generally 1 to 200 grams per 100 kg seed, preferably 5 to 150 grams per 100 kg seed (10 to 10 per 100 kg seed). 100 grams, etc.).

  The term seed includes, but is not limited to, true seeds, seed pieces, suckers, corn grains, bulbs, fruits, tubers, grains, rhizomes, cuttings, cut shoots, and the like. It encompasses all kinds of seeds and plant pearls, and in a preferred embodiment means authentic seeds.

  The invention also includes seeds that are coated or treated with a compound of formula I. The term “coated or treated with and / or containing” generally means that the active ingredient is mostly on the surface of the seed at the time of application, but depending on the method of application, a part of the ingredient However, it shows that it can penetrate into the seed material to some extent. When the seed product is planted (again), it can absorb the active ingredient. In one embodiment, the present invention makes available a plant propagation material to which a compound of formula (I) is attached. In addition, this makes available compositions comprising plant propagation material treated with a compound of formula (I).

  Seed treatment includes all suitable seed treatment techniques known in the art such as seed dressing, seed coating, seed dispersal, seed soaking and seed pelleting. Seed treatment application of the compound of formula (I) may be performed by any known method, such as by spraying or spraying seeds before sowing or during sowing / seed planting.

Biological examples:
Example B1: Activity against Egyptian Littoralis (Egyptian Yeast) (Larvicide, Feeding / Residual Contact Activity, Prevention)
Cotton leaf pieces were placed on agar in a 24-well microtiter plate and sprayed with the test solution. After drying, the leaf pieces were infested with 5 L1 larvae. Samples were examined for mortality, repellent effects, feeding behavior, and growth regulation 3 days after treatment (DAT). Control of Egyptian Littoralis with a test sample is when at least one of mortality, feeding inhibition effects, and growth inhibition is higher than untreated samples.

  In this test, compounds P1, P2, P3, P4, P5, P6, P7, P8, P9, P10, P11, P12, P13, P14, P15, P17, P18, P22, P23, P24, P25, P28, P29 , P30, P33, P35, P38, P39, P40, P41, P43, P44, P45, P47, P48, P49, P50, P51, P52, P53 and P54 are in three categories (mortality, Showed at least 80% effect in at least one of (feeding inhibition or growth inhibition).

Example B2: Activity against Spodoptera littoralis (Egyptian salmon) (systemic activity)
Test compounds were pipetted into 24-well plates and mixed with agar. Lettuce seeds are placed on agar and the multiwell plate is closed by another plate that also contains agar. After 7 days, the roots had absorbed the compound and lettuce had grown into the lid plate. Here, lettuce leaves were cut out and placed in a lid plate. Spodoptera eggs were pipetted onto a wet gel blotting paper through a plastic stencil and the plate was closed with this blotting paper. Samples are examined for mortality, repellency, feeding behavior, and growth regulation after 5 days of infestation.

  In this test, compounds P2, P3, P4, P9, P10, P12 and P15 are at least in at least one of the three categories (mortality, feeding inhibition, or growth inhibition) at a concentration of 12.5 ppm. An effect of 80% was shown.

Example B3: Activity against Platypus xylostella (Larvae) (larvacidal, feeding / residual contact activity, prevention)
A 24-well microtiter plate (MTP) with artificial feed was treated with the test solution by pipette. After drying, the MTP was infested with L2 larvae (10-15 per well). After a 5-day incubation period, the samples were examined for larval mortality, feeding inhibition and growth regulation.

  In this test, compounds P2, P4, P6, P9, P10, P11, P12, P15, P17, P18, P23, P24, P25, P28, P29, P33, P35, P38, P39, P40, P43, P44, P45 , P48, P49, P50, P51, P52, P53 and P54 showed activity of over 80% at a concentration of 400 ppm.

Example B4: Activity against Diabrotica balteata (corn beetle) (larvae L2 in corn shoots, feeding / contact, prevention)
Corn buds placed on the agar layer in a 24-well microtiter plate were treated with the test solution by spraying. After drying, MTP was infested with L2 larvae (6-10 per well). After a 5-day incubation period, the samples were examined for larval mortality and growth regulation.

  In this test, compounds P1, P2, P3, P4, P6, P7, P9, P10, P11, P12, P15, P16, P17, P18, P20, P22, P23, P24, P25, P26, P28, P29, P30 , P32, P33, P34, P35, P36, P38, P39, P40, P41, P43, P44, P45, P47, P48, P49, P50, P51, P52, P53, and P54 exceed 80% at a concentration of 400 ppm Showed activity.

Example B5: Activity against peach persicae (peach aphid) (feeding / residual contact activity, prevention), mixed population Sunflower leaf pieces are placed on agar in a 24-well microtiter plate and tested solution Sprayed. After drying, the leaf pieces were infested with aphid populations of various ages. After a 6 DAT incubation period, the samples were examined for mortality and special effects (eg phytotoxicity).

  In this test, compounds P1, P2, P3, P4, P5, P6, P8, P9, P10, P11, P14 and P15 showed an activity of over 80% at a concentration of 400 ppm.

Example B6: Activity against peach persicae (peach aphid) (feeding activity Sachet test), mixed population Test compounds are placed by pipette into 24-well plates and mixed with sucrose solution did. The plate was closed with stretched parafilm. A plastic stencil with 24 holes was placed on the plate and the infested pea seedlings were placed directly on the parafilm. The infested plate was closed with gel blotting paper and another plastic stencil and then turned upside down. Five days after infestation, the samples were examined for mortality. Application rate: 12.5 ppm.

  In this test, compounds P1, P2, P23, P25, P38, P39, P40, P41, P43, P45, P50 and P54 showed at least 80% activity at a concentration of 12.5 ppm.

Example B7: Activity against Tobacco whiteflies (adulticide contact activity, prevention), adult cotton leaf pieces were placed on agar in a 24-well microtiter plate and sprayed with the test solution. After drying, this leaf piece was infested with whitefly adults. After an incubation period of 7 DAT, the samples were examined for mortality and special effects (eg phytotoxicity).

  In this test, compounds P2, P4, P6, P9, P10 and P15 showed an activity of over 80% at a concentration of 400 ppm.

Example B8: Activity against Euschistus heros (Neotropical Brown Stink Bug) Prepared from 10'000 ppm DMSO stock solution on soybean leaves on agar in 24-well microtiter plates The test aqueous solution was sprayed. After drying, the leaves were infested with N-2 nymphs. Samples were evaluated for mortality 5 days after infestation.

  In this test, compounds P2, P4, P8, P15, P25, P29, P35, P38 and P40 showed an activity of over 80% at a concentration of 400 ppm.

Example B9: Activity against peach peach aphid (my peach aphid) (systemic / feeding activity, treatment), mixed population Roots of pea seedlings infested with aphid populations of various ages Was placed directly into the test solution. Six days after introduction, samples were examined for mortality and special effects on plants.

  In this test, compounds P4, P39, P50 and P54 showed at least 80% activity at a concentration of 24 ppm.

Example B10: Activity against Tetranychus urticae (Spotted spider mite) Kidney leaf pieces on agar in 24-well microtiter plates were sprayed with an aqueous test solution prepared from a 10'000 ppm DMSO stock solution. After drying, the leaf pieces were infested with tick populations of various ages. Samples were evaluated for mortality in mixed populations (moving state) 8 days after infestation.

  The following compound: P3 resulted in at least 80% mortality at an application rate of 400 ppm.

Example B11: Activity against Aedes aegypti (yellow fever mosquito) The test solution was placed in a 12-well tissue culture plate at a dosage of 200 ppm in ethanol. After the sediment was dried, five, 2-5 day old female adult Aedes aegypti were added to each well and grown in a 10% sucrose solution in cotton wool mass. Knockdown assessments were made 1 hour after introduction and mortality was assessed 24 and 48 hours after introduction.

  The following compounds: P3, P4 and P9 showed at least 80% control of Aedes aegypti after 48 hours.

Claims (15)

Formula I

(Where
G ₁ is nitrogen or CR ₂ ;
G ₂ is nitrogen or CR ₃ ;
G ₃ is nitrogen or CR ₄ ;
G ₄ is nitrogen or CR ₅ ;
G ₅ is nitrogen or CR ₆ , provided that no more than 2 nitrogens may follow as G;
_{R 2, R 3, R 4} , R 5 or R _6, independently of one another, hydrogen, halogen, C ₁ -C ₄ haloalkyl, one or two C ₁ -C ₄ haloalkyl substituted with hydroxy, 1 one or C ₁ -C ₄ haloalkyl substituted with two methoxy, C ₁ -C ₄ haloalkyl substituted with one or two cyano; or _{R 2, R 3, R 4} , R 5 or R ₆ but independently of one another, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, O (C ₁ ~C ₄ haloalkyl), SF _5, phenylcarbonyl thio, cyano, Mercapto, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylcarbonyl or C (O) C ₁ -C ₄ haloalkyl; or two adjacent R _i, where R _i is R ₂ , R _{2 3,} R _4, R ₅ and R ₆ Al is selected), together, fragments -OCH ₂ O-or may form a OCF ₂ O-;
Q is the formula Q ₁ and Q ₂

A group selected from the group consisting of:
Where the arrow indicates the point of attachment to the imidazole ring;
X is S, SO or SO ₂ ;
Each R is, independently of one another are hydrogen, halogen, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkyl;
Each R ₁ independently of _one another is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C _3- C ₆ halocycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl or C ₂ -C ₆ alkynyl; and each R ₇ independently of one another is hydrogen or halogen;
R ₈ is hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; and R ₉ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or halogen), And agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the above compounds (provided that 2- [5-methyl-4- (3-pyridyl) -1H-imidazole- Except 2-yl] -3-methylsulfanyl-pyridine). Formula I-1

(Where
G ₁ , G ₂ , G ₃ , G ₄ , and G ₅ are as defined by formula I in claim 1;
X ₁ is S, SO or SO ₂ ;
Ra ₁ is hydrogen, halogen or C ₁ -C ₄ haloalkyl;
R ₁₁ is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;
R ₈ is as defined by formula I in claim 1;
R ₉ is, agrochemically acceptable salts of the compounds, as well as the compound of formula I according to claim 1 represented by are as defined above) in Formula I in Claim 1, stereoisomer , Enantiomers, tautomers and N-oxides. G ₁ is CH, G ₂ is CH, G ₃ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃ ) A compound of formula I-1 according to claim 2, wherein C, (SO ₂ CF ₃ ) or C (halogen), G ₄ is CH, and G ₅ is CH. G ₁ is CH, and G ₂ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃ ) Or C (halogen), G ₃ is CH, G ₄ is CH, and G ₅ is CH. Formula I-2

(Where
G ₁ , G ₂ , G ₃ , G ₄ , and G ₅ are as defined by formula I in claim 1;
X ₂ is S, SO or SO ₂ ;
Ra ₂ is hydrogen, halogen or C ₁ -C ₄ haloalkyl;
R ₁₂ is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;
R ₈ is as defined by formula I in claim 1;
R ₉ is as defined above for Formula I in Claim 1), as well as an agrochemically acceptable salt, stereoisomer of said compound, and Enantiomers, tautomers and N-oxides. G ₁ is CH, G ₂ is CH, and G ₃ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃₎ a C (SO ₂ CF ₃₎ or C (halogen), G ₄ is is CH, and G ₅ are CH, and compounds of formula I-2 according to claim 5. G ₁ is CH, and G ₂ is C (CF ₃ ), C (OCF ₃ ), C (CN), C (C (O) CH ₃ ), C (SCF ₃ ), C (SO ₂ CF ₃₎ or a C (halogen), G ₃ is CH, and G ₄ are CH, and and G ₅ is CH, and compounds of formula I-2 according to claim 5. Formula I-3

(Where
A is N or CH;
R ₁₀ is mono- or polysubstituted with a substituent independently selected from the group consisting of halogen, cyano, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkylcarbonyl. phenyl or R ₁₀ is mono-substituted by C ₁ -C ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ substituents independently selected from the group consisting of halo alkylsulfonyl; phenyl Or R ₁₀ is phenyl substituted with the fragment —OCF ₂ O— at _two adjacent positions; or R ₁₀ is halogen, cyano, C ₁ -C ₄ haloalkoxy, C ₁ -C _4. with substituents selected independently from the group consisting of haloalkyl and C ₁ -C ₄ alkylcarbonyl be mono- or polysubstituted by pyridyl; or R ₁₀ is, C ₁ -C ₄ Haroa Kirusurufaniru, be a C ₁ -C ₄ haloalkylsulfinyl and C ₁ -C ₄ pyridyl which is monosubstituted with a substituent selected independently from the group consisting of halo alkylsulfonyl; or R ₁₀ is, in two adjacent positions fragment -OCF pyridyl substituted ₂ O- in;
X ₃ is S, SO or SO ₂ ;
Ra ₃ is hydrogen or C ₁ -C ₄ haloalkyl;
R ₁₃ is C ₁ -C ₄ alkyl;
R ₈ is hydrogen or C ₁ -C ₄ alkyl; and R ₉ is hydrogen, represented by compounds of C ₁ -C ₄ alkyl or halogen), the compound of formula I according to claim 1 . Formula I-4

(Where
A is N or CH;
R _{10 ′} is a formula DA1 to DA5

A diazine group selected from the group consisting of: wherein the arrow indicates the point of attachment to the triazole ring, and the group R ₁₀ ′ is halogen, cyano, C ₁ -C ₄ haloalkoxy and C _1- May be mono- or poly-substituted with a substituent independently selected from the group consisting of C ₄ haloalkyl;
X ₄ is S, SO or SO ₂ ;
Ra ₄ is hydrogen or C ₁ -C ₄ haloalkyl;
R ₁₄ is C ₁ -C ₄ alkyl;
R ₈ is hydrogen or C ₁ -C ₄ alkyl; and R ₉ is hydrogen, represented by compounds of C ₁ -C ₄ alkyl or halogen), the compound of formula I according to claim 1 .   As an active ingredient at least one compound of formula I according to claim 1, or optionally a tautomer thereof, in free form or in an agrochemically usable salt form, respectively, and at least one auxiliary agent; A pesticide composition comprising:   A method for controlling pests, comprising the step of applying the composition of claim 10 to the pests or their environment, for the treatment of the human or animal body by surgery or treatment. A method, excluding methods and diagnostic methods carried out in the human or animal body.   11. A method for protecting plant propagation material from attack by pests, the method comprising treating the propagation material or a place where the propagation material is planted with the composition of claim 10.   A plant propagation material treated according to the method of claim 12. Formula (IIIa)

(Where
Q and R ₈ are as defined in formula I in claim 1;
R ₉ is hydrogen; and L _G A compound of the it) iodine or bromine. Formula (IVa)

(Where
Q and R ₈ are as defined in formula I in claim 1; and R ₉ is hydrogen).